EP4731635A1 - Chiral iridium hydride catalysts for enantioselective hydrogenation of 4-substituted 1,2- dihydroquinolines - Google Patents

Chiral iridium hydride catalysts for enantioselective hydrogenation of 4-substituted 1,2- dihydroquinolines

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Publication number
EP4731635A1
EP4731635A1 EP24732726.5A EP24732726A EP4731635A1 EP 4731635 A1 EP4731635 A1 EP 4731635A1 EP 24732726 A EP24732726 A EP 24732726A EP 4731635 A1 EP4731635 A1 EP 4731635A1
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European Patent Office
Prior art keywords
alkyl
substituted
group
alkoxy
phenyl
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EP24732726.5A
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German (de)
French (fr)
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Christoph SCHOTES
Christoph Kubis
Dilver Peña FUENTES
Benedict LEIDECKER
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention relates to chiral iridium hydride complexes comprising a) chiral (P,N)-ligand and b) a stabilizing enone ligand of formula (I) wherein R1 is selected from the group consisting of hydrogen, C1-C500-alkyl, C2-C500-alkenyl, C1-C500- alkoxy, C2-C500-alkenyloxy, C1-C500-alkylamino, C2-C500-alkenylamino, di-(C1-C500- alkyl)amino, di-(C2-C500-alkenyl)amino, N-(C1-C500-alkyl)-N-(C2-C500-alkenyl)amino, C3-C8- cycloalkyl, C3-C8 -cycloalkoxy, C3-C8-cycloalkylamino, N-(C1-C500-alkyl)-N-(C3-C8- cycloalkyl)amino, C6-C14-aryl, which may be substituted as further defined in the specification, R1a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6 -alkylcarbonyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a C5-C7-cycloalkanone ring, wherein the C5-C7-cycloalkanone ring is unsubstituted or substituted by one to four substituents selected independently from each other from C1-C6- alkyl, and benzylidene, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, R2 is selected from the group consisting of hydrogen, C1-C500-alkyl, C1-C500-; C1-C500- alkylamino, di-(C1-C500-alkyl)amino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8- cycloalkylamino, N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl)amino, C6-C14-aryl, which may be substituted as further defined in the specification, and the arrow indicates a bond to the iridium atom, as well as to a process for preparing optically active 4-substituted 1,2,3,4-tetrahydroquinolines by enantioselective hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines in presence of such chiral iridium hydride complex.

Description

BCS233012 Foreign Countries FP/Ho 2024-06-03 - 1 - Chiral iridium hydride catalysts for enantioselective hydrogenation of 4-substituted 1,2- dihydroquinolines The invention relates to chiral iridium hydride complexes comprising a) a chiral chelating ligand comprising at least one phosphorus atom and at least one nitrogen atom that both bind to the iridium atom - in the following also referred to as “chiral (P,N)-ligand” - and b) a stabilizing enone ligand of formula (I) as defined below, as well as to a process for preparing optically active 4-substituted 1,2,3,4-tetrahydroquinolines by enantioselective hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines in presence of said complex. 4-Substituted 1,2,3,4-tetrahydroquinolines are versatile intermediates in the synthesis of N-indanyl heteroaryl carboxamide fungicides, including the recently launched pyrazole carboxamide fungicide inpyrfluxam (EP 0 654464, WO 2015/141564, WO 2019/185541, WO 2021/058457, WO 2021/058458). They can be obtained by hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines. WO 2015/141564 describes a process for preparing optically active 4-substituted 1,2,3,4-tetrahydroquinolines, which process comprises the hydrogenation of the corresponding 4-substituted 1,2-dihydroquinolines in presence of a transition metal catalyst having an optically active ligand. The asymmetric hydrogenation of 4- substituted NH-dihydroquinolines proceeded with moderate conversion rates (up to 62.6%) and enantioselectivity (up to 71.3% ee), whereas hydrogenation of N-acetyl-dihydroquinolines gave even poorer conversion (up to 14%) and enantioselectivity (up to 31% ee). WO 2019/185541, WO 2021/058457 and WO 2021/058458 disclose enantioselective hydrogenation of 4- substituted 1,2-dihydroquinolines in presence of a specific chiral iridium (P,N)-ligand catalyst which provides improved conversion rates and enantioselectivity. The chiral iridium (P,N)-ligand catalysts show excellent catalytic activity. However, recovery and recycling of the spent catalyst proved to be difficult. Iridium is a scarce and expensive metal and synthesis of the respective chiral iridium (P,N)-ligand catalysts is complex. Hence, recycling of the catalyst would be highly desirable, in particular in an industrial scale production process in the agrochemicals field. Müller et al. report in Müller, M.-A.; Gruber, S.; Pfaltz, A., Recovery and Recycling of Chiral Iridium (N,P Ligand) Catalysts from Hydrogenation Reactions, Adv. Synth. Catal.2018, 360 (7), 1340-1345, the recovery of chiral iridium (N,P)-ligand catalysts, comprising besides a chiral iridium (N,P)-ligand a stabilizing 1,5- cyclooctadiene ligand, by adding cyclooctadiene to the spent catalyst after the hydrogenation reaction in order to rebuild the initial, stabilized catalyst. The recovered catalyst is isolated and reused, showing essentially the same reactivity and enantioselectivity as the original catalyst. BCS233012 FC -2- Unfortunately, this procedure is not suitable for recovery and recycling of the chiral iridium (P,N)-ligand catalysts disclosed in WO 2019/185541, WO 2021/058457 and WO 2021/058458, since a) reaction of the spent catalyst with cyclooctadiene proceeds too slowly to be suitable for an industrial scale process, and b) isolation and purification of the recovered catalyst as proposed by Müller et al. requires column chromatography (see Müller, Experimental Section), which again is not suitable for larger catalyst amounts necessary for an industrial scale process. Hence, there is need for catalysts that can be easily recycled. Therefore, it is an object of the present invention to provide chiral iridium (P,N)-ligand catalysts for the enantioselective hydrogenation of 4-substituted 1,2- dihydroquinolines that show at least the same level of reactivity and enantioselectivity in said hydrogenation as the catalysts known from WO 2019/185541, WO 2021/058457 and WO 2021/058458, but can be customized more flexibly than the known catalysts, which comprise a stabilizing diene ligand, usually 1,5- cyclooctadiene. Only few suitable diene ligands are available. Mostly 1,5-cyclooctadiene is used, sometimes norbornadiene. Derivatization thereof is rather complex. Catalysts that can be flexibly customized, allow for fine-tuning of important properties, like polarity, solubility in various solvents, stability, and speed of activation, which can be used to arrive at improved recoverability and recyclability. The object described above is achieved by chiral iridium hydride complexes, comprising a) a chiral chelating ligand, wherein said chiral chelating ligand comprises at least one phosphorus atom and at least one nitrogen atom that both bind to the iridium atom, i.e. a chiral (P,N)-ligand, and b) an enone ligand of formula (I), 1 0 wherein R1 is selected from the group consisting of hydrogen, C1-C500-alkyl, C2-C500-alkenyl, C1- C500-alkoxy, C2-C500-alkenyloxy, C1-C500-alkylamino, C2-C500-alkenylamino, di-(C1- C500-alkyl)amino, di-(C2-C500-alkenyl)amino, N-(C1-C500-alkyl)-N-(C2-C500- BCS233012 FC -3- alkenyl)amino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkylamino, N-(C1- C500-alkyl)-N-(C3-C8-cycloalkyl)amino, C6-C14-aryl, wherein C1-C500-alkyl, C2-C500-alkenyl, C1-C500-alkoxy, C2-C500-alkenyloxy, C1-C500- alkylamino, C2-C500-alkenylamino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8- cycloalkylamino and the C1-C500-alkyl, C2-C500-alkenyl and C3-C8-cycloalkyl residues in the di-(C1-C500-alkyl)amino, di-(C2-C500-alkenyl)amino, N-(C1-C500-alkyl)-N-(C2- C500-alkenyl)amino and N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl)amino moieties, are unsubstituted or substituted by substituent(s) independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500-haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1- C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1- C500-alkoxy and C1-C500-haloalkoxy, R1a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a C5-C7-cycloalkanone ring, preferably a cyclohexanone ring, wherein the C5-C7-cycloalkanone ring is unsubstituted or substituted by one to four substituents selected independently from each other from C1-C6-alkyl, and benzylidene, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, R2 is selected from the group consisting of hydrogen, C1-C500-alkyl, C1-C500-alkoxy, C1- C500-alkylamino, di-(C1-C500-alkyl)amino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3- C8-cycloalkylamino, N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl)amino, C6-C14-aryl, wherein C1-C500-alkyl, C1-C500-alkoxy, C1-C500-alkylamino, C3-C8-cycloalkyl, C3-C8- cycloalkoxy, C3-C8-cycloalkylamino and the C1-C500-alkyl and C3-C8-cycloalkyl residues in the di-(C1-C500-alkyl)amino and N-(C1-C500-alkyl)-N-(C3-C8- cycloalkyl)amino moieties, are unsubstituted or substituted by substituent(s) BCS233012 FC -4- independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500-haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1- C500-alkoxy and C1-C500-haloalkoxy, and the arrow indicates a bond to the iridium atom. Contrary to the stabilizing diene ligand present in the catalysts disclosed in WO 2019/185541, WO 2021/058457 and WO 2021/058458, a wide variety of precursors of ligands of formula (I) can be easily synthesized by established processes, for example by reacting readily available aldehydes and ketones as shown in scheme 1. Scheme 1: 0 0 0 1 R2 Surprisingly, on same level as the catalysts known from WO 2019/185541, WO 2021/058457 and WO 2021/058458, while accessibility to many ligands of formula (I) provides the necessary flexibility to fine-tune important characteristics in order to facilitate recovery and recycling of the chiral iridium hydride complex from the spent catalyst. Definitions In the definitions of the symbols given in the above and below formulae, collective terms were used, which are generally representative of the following substituents: Halogen: fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and more preferably fluorine or chlorine. BCS233012 FC -5- Alkyl: saturated, straight-chain or branched hydrocarbyl substituents having 1 to 500, e.g. 1 to 6 or 1 to 4 carbon atoms, for example (but not limited to) C1-C6-alkyl such as methyl, ethyl, propyl (n-propyl), 1- methylethyl (iso-propyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), 1,1- dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1- ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3- methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2- trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Particularly, said group is a C1-C4-alkyl group, e.g. a methyl, ethyl, propyl, 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl), 2- methylpropyl (iso-butyl) or 1,1-dimethylethyl (tert-butyl) group. This definition also applies to alkyl as part of a composite substituent, for example C3-C6-cycloalkyl-C1-C4-alkyl, C6-C14-aryl-C1-C4-alkyl etc., unless defined elsewhere. Alkenyl: unsaturated, straight-chain or branched hydrocarbyl substituents having 2 to 500, e.g.2 to 6 or 2 to 4 carbon atoms and one double bond in any position, for example (but not limited to) C2-C6-alkenyl such as vinyl, allyl, (E)-2-methylvinyl, (Z)-2-methylvinyl, isopropenyl, homoallyl, (E)-but-2-enyl, (Z)-but-2-enyl, (E)-but-1-enyl, (Z)-but-l-enyl, 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-methylprop-1-enyl, (E)-1- methylprop-1-enyl, (Z)-1-methylprop-1-enyl, pent-4-enyl, (E)-pent-3-enyl, (Z)-pent-3-enyl, (E)-pent-2-enyl, (Z)-pent-2-enyl, (E)-pent-l-enyl, (Z)-pent-l-enyl, 3- methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3- enyl, 3-methylbut-2-enyl, (E)-2-methylbut-2-enyl, (Z)-2-methylbut-2-enyl, (E)-1-methylbut-2-enyl, (Z)-1- methylbut-2-enyl, (E)-3-methylbut-1-enyl, (Z)-3-methylbut-1-enyl, (E)-2- methylbut-1-enyl, (Z)-2- methylbut-1-enyl, (E)-1-methylbut-1-enyl, (Z)-1- methylbut-1-enyl, 1,1-dimethylprop-2-enyl, 1-ethylprop-1- enyl, 1-propylvinyl, 1- isopropylvinyl, (E)-3,3-dimethylprop-1-enyl, (Z)-3,3-dimethylprop-1-enyl, hex-5- enyl, (E)-hex-4- enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3-enyl, (E)-hex-2-enyl, (Z)-hex-2-enyl, (E)- hex-l-enyl, (Z)-hex-l-enyl, 4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1- methylpent-4- enyl, 4-methylpent-3-enyl, (E)-3-methylpent-3-enyl, (Z)-3- methylpent-3-enyl, (E)-2-methylpent-3-enyl, (Z)- 2-methylpent-3-enyl, (E)-1- methylpent-3-enyl, (Z)-1 -methylpent-3-enyl, (E)-4-methylpent-2-enyl, (Z)-4- methylpent-2-enyl, (E)-3-methylpent-2-enyl, (Z)-3-methylpent-2-enyl, (E)-2- methylpent-2-enyl, (Z)-2- methylpent-2-enyl, (E)-1 -methylpent-2-enyl, (Z)-1- methylpent-2-enyl, (E)-4-methylpent-1-enyl, (Z)-4- methylpent-1-enyl, (E)-3- methylpent-1-enyl, (Z)-3-methylpent-1 -enyl, (E)-2-methylpent-1 -enyl, (Z)-2- methylpent-1-enyl, (E)-1-methylpent-1-enyl, (Z)-1-methylpent-1-enyl, 3-ethylbut- 3-enyl, 2-ethylbut-3-enyl, 1-ethylbut-3-enyl, (E)-3-ethylbut-2-enyl, (Z)-3-ethylbut-2-enyl, (E)-2-ethylbut-2-enyl, (Z)-2-ethylbut-2-enyl, (E)-1-ethylbut-2-enyl, (Z)-1-ethylbut-2-enyl, (E)-3-ethylbut-1-enyl, (Z)-3-ethylbut-1-enyl, 2-ethylbut-1-enyl, (E)-1-ethylbut-1-enyl, (Z)-1-ethylbut-1-enyl, 2-propylprop-2-enyl, 1-propylprop-2- enyl, 2-isopropylprop-2- enyl, 1 -isopropylprop-2-enyl, (E)-2-propylprop-1-enyl, (Z)- 2-propylprop-1-enyl, (E)-1-propylprop-1-enyl, (Z)-1-propylprop-1-enyl, (E)-2- isopropylprop-1-enyl, (Z)-2-isopropylprop-1-enyl, (E)-1-isopropylprop-1- BCS233012 FC -6- enyl, (Z)-1- isopropylprop-1-enyl, 1-(1,1-dimethylethyl)ethenyl, buta-1,3-dienyl, penta-1,4-dienyl, hexa-1,5- dienyl or methylhexadienyl. Particularly, said group is vinyl or allyl. This definition also applies to alkenyl as part of a composite substituent unless defined elsewhere. Alkynyl: straight-chain or branched hydrocarbyl substituents having 2 to 6, preferably 2 to 4 carbon atoms and one triple bond in any position, for example (but not limited to) C2-C6-alkynyl, such as ethynyl, prop-1- ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methylprop-2-ynyl, pent-1-ynyl, pent-2-ynyl, pent- 3-ynyl, pent-4-ynyl, 2-methylbut-3-ynyl, 1 -methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1- ethylprop-2-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 3-methylpent-4-ynyl, 2- methylpent-4-ynyl, 1-methylpent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methylpent-2-ynyl, 4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1-ethylbut-3-ynyl, 1- ethylbut-2-ynyl, 1-propylprop-2-ynyl, 1-isopropylprop-2-ynyl, 2,2-dimethylbut-3-ynyl, 1,1-dimethylbut-3- ynyl, 1,1-dimethylbut-2-ynyl, or 3,3-dimethylbut-1-ynyl group. Particularly, said alkynyl group is ethynyl, prop-1-ynyl, or prop-2-ynyl. This definition also applies to alkynyl as part of a composite substituent unless defined elsewhere. Haloalkyl: straight-chain or branched alkyl substituents having 1 to 500, e.g.1 to 6 or 1 to 4 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as specified above, for example (but not limited to) C1-C3-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2- fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as part of a composite substituent unless defined elsewhere. Haloalkenyl and haloalkynyl are defined analogously to haloalkyl except that, instead of alkyl groups, alkenyl and alkynyl groups are present as part of the substituent. Alkoxy: saturated, straight-chain or branched alkoxy substituents having 1 to 500, e.g.1 to 6 or 1 to 4 carbon atoms, for example (but not limited to) C1-C6-alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2- dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1- ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. This definition also applies to alkoxy as part of a composite substituent unless defined elsewhere. BCS233012 FC -7- Haloalkoxy: straight-chain or branched alkoxy substituents having 1 to 500, e.g.1 to 6 or 1 to 4 carbon atoms carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as specified above, for example (but not limited to) C1-C3-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1- fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro- 2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1- trifluoroprop-2-oxy. This definition also applies to haloalkoxy as part of a composite substituent, unless defined elsewhere. Alkenyloxy: The term “alkenyloxy” as used herein refers to a formula (alkenyl)-O-, in which the term "alkenyl” group has the meaning as defined herein. Examples of C2-C6-alkenyloxy include but are not limited to ethenyloxy (or "vinyloxy"), prop-2-en-1-yloxy (or "allyloxy"), prop-1-en-1-yloxy, prop-1-en-2-yloxy (or "isopropenyloxy"), but-3-enyloxy, but-2-enyloxy, but-1-enyloxy, 2-methylprop-2-enyloxy, 1-methylprop-2- enyloxy, 2-methylprop-1-enyloxy and 1-methylprop-1-enyloxy. Alkylamino: monoalkylamino or dialkylamino, wherein monoalkylamino represents an amino radical having one alkyl residue with 1 to 500, e.g.1 to 6 carbon atoms attached to the nitrogen atom. Non-limiting examples include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino and tert-butylamino, and wherein dialkylamino represents an amino radical having two independently selected alkyl residues with 1 to 500, e.g. 1 to 6 carbon atoms each attached to the nitrogen atom. Non-limiting examples include N,N-di- methylamino, N,N-diethylamino, N,N-diisopropylamino, N-ethyl-N-methylamino, N-methyl-N-n-propyl- amino, N-isopropyl-N-n-propylamino and N-tert-butyl-N-methylamino. Alkenylamino is defined analogously to alkylamino except that, instead of alkyl groups, alkenyl groups are present as part of the substituent. The term “C1-C6-alkylcarbonyl” as used herein refers to a linear or branched group of formula (C1-C6-alkyl)- C(=O)-, in which the term "C1-C6-alkyl" is as defined herein. Cycloalkyl: mono- or polycyclic, saturated hydrocarbyl substituents having 3 to 12, preferably 3 to 8 and more preferably 3 to 6 carbon ring members, for example (but not limited to) cyclopropyl, cyclopentyl, cyclohexyl and adamantyl. This definition also applies to cycloalkyl as part of a composite substituent, for example C3- C6-cycloalkyl-C1-C4-alkyl, unless defined elsewhere. BCS233012 FC -8- Cycloalkoxy: The term “cycloalkoxy” as used herein refers to a formula (cycloalkyl)-O-, in which the term "cycloalkyl” group has the meaning as defined herein. Examples of C3-C8-cycloalkoxy include but are not limited to cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy. Cycloalkylamino: is defined analogously to alkylamino except that, instead of alkyl groups, cycloalkyl groups are present as part of the substituent. Aryl: mono-, bi- or tricyclic aromatic or partially aromatic substituents having 6 to 14 carbon atoms, for example (but not limited to) phenyl, naphthyl, tetrahydronapthyl, indenyl and indanyl. The binding to the superordinate general structure can be carried out via any possible ring member of the aryl residue. Aryl is preferably selected from phenyl, 1-naphthyl, 2-naphthyl, 9-phenantryl und 9-antracenyl. Phenyl is particularly preferred. The chiral hydride complexes according to the invention comprise an enone ligand of formula (I) o wherein R1, R1a, R2 and the arrow are R1a is preferably selected from the group consisting of hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyl, or R1a and R1 form together with the carbon atom to which R1a is attached, and the carbonyl group to which R1 is attached, a C5-C7-cycloalkanone ring, preferably a cyclohexanone ring, wherein the C5- C7-cycloalkanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C6-alkyl, and C1-C6-alkoxy. R1a is more preferably selected from the group consisting of hydrogen, C1-C4-alkylcarbonyl, or BCS233012 FC -9- R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a C5-C7-cycloalkanone ring, preferably a cyclohexanone ring, wherein the C5- C7-cycloalkanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C6-alkyl, and C1-C6-alkoxy. R1a is even more preferably selected from the group consisting of hydrogen and acetyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1- C6-alkyl, and C1-C6-alkoxy. R1a is even more preferably selected from the group consisting of hydrogen and acetyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted. In one embodiment R1a is acetyl, i.e. the chiral iridium hydride complex comprises an enone ligand of formula (I-Ac) o wherein R1, R2 and the arrow are BCS233012 FC -10- In another embodiment R1a is hydrogen, i.e. the chiral iridium hydride complex comprises an enone ligand of formula (I-H) o (I-H) wherein R1, R2 and the arrow are defined as indicated above. In another embodiment R1a and R1 form together with the carbon atom to which R1a is attached, and the carbonyl group to which R1 is attached, a cyclopentanone ring, cyclohexanone ring or cycloheptanone ring, preferably a cyclohexanone ring, wherein the cyclopentanone ring, cyclohexanone ring or cycloheptanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from methyl, ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2- methylpropyl (iso-butyl), 1,1-dimethylethyl (tert-butyl), methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy. Preferably, the benzylidene group is unsubstituted or substituted by one, two or three substituents selected independently from each other from methyl, ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), methoxy, ethoxy, propoxy, and 1-methylethoxy. More preferably, the benzylidene group is unsubstituted or substituted by one, two or three substituents selected independently from each other from methyl, ethyl, methoxy, and ethoxy. More preferably, the benzylidene group is unsubstituted or substituted by one, two or three substituents selected independently from each other from methyl, and methoxy. More preferably, the benzylidene group is unsubstituted or substituted by one substituent selected from methyl, and methoxy. More preferably, the benzylidene group is unsubstituted. The preferred and more preferred definitions of R1 and R2 as indicated below apply to enone ligands of formula (I), including enone ligands of formula (I-Ac) and enone ligands of formula (I-H). R1 is preferably selected from the group consisting of C1-C500-alkyl, C2-C500-alkenyl, C6-C14-aryl, wherein C1-C500-alkyl and C2-C500-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and BCS233012 FC -11- wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl. R1 is more preferably selected from the group consisting of C1-C400-alkyl, C2-C400-alkenyl, C6-C14-aryl, wherein C1-C400-alkyl and C2-C400-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C400-alkyl, C1-C400-alkoxy, C1-C400-haloalkyl, and C1-C400-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C400-alkyl, C1-C400-haloalkyl. R1 is more preferably selected from the group consisting of C1-C300-alkyl, C2-C300-alkenyl, C6-C14-aryl, wherein C1-C300-alkyl and C2-C300-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C300-alkyl, C1-C300-alkoxy, C1-C300-haloalkyl, and C1-C300-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C300-alkyl, C1-C300-haloalkyl. R1 is more preferably selected from the group consisting of C1-C200-alkyl, C2-C200-alkenyl, C6-C14-aryl, wherein C1-C200-alkyl and C2-C200-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C200-alkyl, C1-C200-alkoxy, C1-C200-haloalkyl, and C1-C200-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C200-alkyl, C1-C200-haloalkyl. R1 is more preferably selected from the group consisting of C1-C150-alkyl, C2-C150-alkenyl, C6-C14-aryl, wherein C1-C150-alkyl and C2-C150-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C150-alkyl, C1-C150-alkoxy, C1-C150-haloalkyl, and C1-C150-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C150-alkyl, C1-C150-haloalkyl. R1 is more preferably selected from the group consisting of C1-C100-alkyl, C2-C100-alkenyl, C6-C14-aryl, BCS233012 FC -12- wherein C1-C100-alkyl and C2-C100-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C100-alkyl, C1-C100-alkoxy, C1-C100-haloalkyl, and C1-C100-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl. R1 is more preferably selected from the group consisting of C1-C100-alkyl, C2-C100-alkenyl, phenyl, wherein C1-C100-alkyl and C2-C100-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C100-alkyl, C1-C100-alkoxy, C1-C100-haloalkyl, and C1-C100-haloalkoxy, and wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl. R1 is more preferably selected from the group consisting of C1-C100-alkyl, C2-C100-alkenyl, phenyl, wherein C1-C100-alkyl and C2-C100-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy and wherein in case R1 is phenyl, this phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl. R1 is more preferably selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, phenyl, wherein C1-C6-alkyl and C2-C6-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and wherein in case R1 is phenyl, this phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl. R1 is more preferably selected from the group consisting of C1-C3-alkyl, vinyl, phenyl, wherein the vinyl is unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1- C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and BCS233012 FC -13- wherein in case R1 is phenyl, this phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, and C1-C100-haloalkyl, preferably from the group consisting of C1-C3-alkyl. R1 is more preferably selected from the group consisting of methyl and vinyl, wherein the vinyl is unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1- C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy. R1 is more preferably selected from the group consisting of methyl and vinyl, wherein the vinyl is substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C100-alkyl, C1-C100- alkoxy, C1-C100-haloalkyl, and C1-C100-haloalkoxy. R1 is more preferably selected from the group consisting of methyl and vinyl, wherein the vinyl is substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one, two or three substituents selected independently from each other from methyl, ethyl, propyl (n- propyl), 1-methylethyl (iso-propyl), methoxy, ethoxy, propoxy, and 1-methylethoxy, preferably from methyl and methoxy. R1 is also more preferably selected from the group consisting of methyl, vinyl and phenyl, wherein the vinyl is substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one, two or three substituents selected independently from each other from methyl, ethyl, propyl (n- propyl), 1-methylethyl (iso-propyl), methoxy, ethoxy, propoxy, and 1-methylethoxy, preferably from methyl and methoxy, more preferably from methoxy, and wherein in case R1 is phenyl, this phenyl is unsubstituted. R2 is preferably selected from the group consisting of C1-C500-alkyl, C6-C14-aryl, wherein C1-C500-alkyl is unsubstituted or substituted by substituent(s) independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500-haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and BCS233012 FC -14- wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1-C500-alkoxy and C1-C500- haloalkoxy. R2 is more preferably C6-C14-aryl, wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1-C500-alkoxy and C1-C500- haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1-C500-alkoxy and C1-C500-haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C400-alkyl, C1-C400-haloalkyl, C1-C400-alkoxy and C1-C400-haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C300-alkyl, C1-C300-haloalkyl, C1-C300-alkoxy and C1-C300-haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C200-alkyl, C1-C200-haloalkyl, C1-C200-alkoxy and C1-C200-haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C150-alkyl, C1-C150-haloalkyl, C1-C150-alkoxy and C1-C150-haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl, C1-C100-alkoxy and C1-C100-haloalkoxy. R2 is more preferably phenyl, BCS233012 FC -15- wherein the phenyl is unsubstituted or substituted by one, two or three substituents selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and C1-C6-haloalkoxy. R2 is more preferably phenyl, wherein the phenyl is unsubstituted or substitu,ted by one, two or three substituents selected from the group consisting of methyl, ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), methoxy, ethoxy, propoxy, and 1-methylethoxy, preferably from methyl and methoxy, more preferably from methoxy. R2 is more preferably phenyl or 4-methoxyphenyl (para-methoxyphenyl). Particularly preferred are chiral iridium hydride complexes comprising an enone ligand of formula (I), wherein R1 is methyl, phenyl, styryl or 4-methoxystyryl (para-methoxystyryl), R1a is hydrogen or acetyl, or R1a and R1 form together with the carbon atom to which R1a is attached, and the carbonyl group to which R1 is attached, a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, and R2 is phenyl or 4-methoxyphenyl (para-methoxyphenyl). Particularly preferred are also chiral iridium hydride complexes comprising an enone ligand of formula (I-H), wherein R1 is methyl or styryl, and R2 is phenyl or 4-methoxyphenyl (para-methoxyphenyl). As outlined above, a wide variety of enone ligands of formula (I) is accessible via established routes. It is for example possible to incorporate long carbon chain residues, e.g. C6-C500-alkyl, C6-C500-alkenyl, C6-C500- alkoxy, C6-C500-alkenyloxy, C6-C500-alkylamino, C6-C500-alkenylamino, di-(C6-C500-alkyl)amino, di-(C6-C500- alkenyl)amino, N-(C6-C500-alkyl)-N-(C6-C500-alkenyl)amino. Presence of at least one such group enhances solubility of the enone and the chiral iridium hydride complex comprising such ligand in non-polar solvents, BCS233012 FC -16- e.g. heptane, allowing recovery of the chiral iridium hydride complex from a reaction mixture by simple extraction with such non-polar solvent. Hence, particularly preferred are also chiral iridium hydride complexes comprising an enone ligand of formula (I), wherein the enone ligand comprises at least one, preferably one, long carbon chain residue selected from the group consisting of C6-C500-alkyl, C6-C500-alkenyl, C6-C500-alkoxy, C6-C500-alkenyloxy, C6-C500- alkylamino, C6-C500-alkenylamino, di-(C6-C500-alkyl)amino, di-(C6-C500-alkenyl)amino and N-(C6-C500- alkyl)-N-(C6-C500-alkenyl)amino. Preferably, the long carbon chain residue is selected from the group consisting of C6-C400-alkyl, C6-C400- alkenyl, C6-C400-alkoxy, C6-C400-alkenyloxy, C6-C400-alkylamino, C6-C400-alkenylamino, di-(C6-C400- alkyl)amino, di-(C6-C400-alkenyl)amino and N-(C6-C400-alkyl)-N-(C6-C400-alkenyl)amino. More preferred, the long carbon chain residue is selected from the group consisting of C10-C300-alkyl, C10- C300-alkenyl, C10-C300-alkoxy, C10-C300-alkenyloxy, C10-C300-alkylamino, C10-C300-alkenylamino, di-(C10- C300-alkyl)amino, di-(C10-C300-alkenyl)amino and N-(C10-C300-alkyl)-N-(C10-C300-alkenyl)amino. More preferred, the long carbon chain residue is selected from the group consisting of C10-C200-alkyl, C10- C200-alkenyl, C10-C200-alkoxy, C10-C200-alkenyloxy, C10-C200-alkylamino, C10-C200-alkenylamino, di-(C10- C200-alkyl)amino, di-(C10-C200-alkenyl)amino and N-(C10-C200-alkyl)-N-(C10-C200-alkenyl)amino. More preferred, the long carbon chain residue is selected from the group consisting of C20-C150-alkyl, C20- C150-alkenyl, C20-C150-alkoxy, C20-C150-alkenyloxy, C20-C150-alkylamino, C20-C150-alkenylamino, di-(C20- C150-alkyl)amino, di-(C20-C150-alkenyl)amino, N-(C20-C150-alkyl)-N-(C20-C150-alkenyl)amino. More preferred, the long carbon chain residue is selected from the group consisting of C20-C100-alkyl, C20- C100-alkenyl, C20-C100-alkoxy, C20-C100-alkenyloxy, C20-C100-alkylamino, C20-C100-alkenylamino, di-(C20- C100-alkyl)amino, di-(C20-C100-alkenyl)amino, N-(C20-C100-alkyl)-N-(C20-C100-alkenyl)amino. Most preferred, the long carbon chain residue is C20-C100-alkyl, e.g. polyisopropylene or polyisobutylene having a respective chain length. Particularly preferred are, therefore, furthermore chiral iridium hydride complexes comprising an enone ligand of formula (I), wherein R1 is methyl, phenyl or styryl, wherein the phenyl and styryl is unsubstituted or substituted by one substituent selected from C20-C100-alkyl, C20-C100-alkoxy, C20-C100-haloalkyl, and C20-C100- haloalkoxy, and BCS233012 FC -17- R2 is phenyl substituted by one substituent selected from C20-C100-alkyl, C20-C100-alkoxy, C20-C100- haloalkyl, and C20-C100-haloalkoxy. Particularly preferred are also chiral iridium hydride complexes comprising an enone ligand of formula (I), wherein R1 is methyl, phenyl or styryl, wherein the phenyl or styryl is unsubstituted or substituted by C20-C100- alkyl, and R2 is phenyl substituted by C20-C100-alkyl. The chiral iridium hydride complexes according to the invention comprise furthermore a chiral chelating ligand, wherein said chiral chelating ligand comprises at least one phosphorus atom and at least one nitrogen atom that both bind to the iridium atom. Such chiral (P,N)-ligands and their interaction with the iridium atom can be schematically depicted as follows: Preferably, the chiral chelating ligand is a ligand of formula (IIa), (IIb), (IIIa), (IIIb), (IVa) or (IVb), BCS233012 FC -18- wherein R3, R4 and R5 are independently from one another selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7- cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl and the C3-C7-cycloalkyl in the C3-C7-cycloalkyl-C1-C4-alkyl moiety are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4- haloalkyl and C1-C4-haloalkoxy, and wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1-C6-alkyl substituents, R6 and R7 are independently from one another selected from the group consisting of C1-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C3-C12- cycloalkyl-C1-C4-alkyl, C6-C14-aryl, C6-C14-aryloxy, C6-C14-aryl-C1-C4-alkyl, piperidinyl and pyridyl, wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and di(C1-C6-alkyl)amino, are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl, C6-C14-aryloxy and C3-C12-cycloalkyl, in each case as such or as part of a composite substituent, are unsubstituted or substituted by one to five substituents selected from the BCS233012 FC -19- group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1-C6-alkyl substituents, or R6 and R7 together with the phosphorus atom which they are bound to, form a phospholane ring, which is unsubstituted or substituted with one or two C1-C6-alkyl groups, or R6 and R7 together form in which the are p and q are independently from one another selected from 0, 1 and 2, R11 and R12 are independently selected from C1-C6-alkyl and phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy and phenyl, which is unsubstituted or substituted by one or two C1-C4-alkyl substituents, m is 1 or 2, R8 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C4-alkyl, C1-C4- alkyl-C3-C7-cycloalkyl, C6-C14-aryl or C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R9 and R10 are independently from one another selected from the group consisting of C1-C6-alkyl, C2- C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C3-C12- cycloalkyl-C1-C4-alkyl, C6-C14-aryl, C6-C14-aryloxy and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and di(C1-C6-alkyl)amino, are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting BCS233012 FC -20- of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, phenyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl, the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl, the C6-C14-aryloxy and C3- C12-cycloalkyl, in each case as such or as part of a composite substituent, are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, phenyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R9 and R10 together with the phosphorus atom which they are bound to, form a phospholane ring, which is unsubstituted or substituted with one or two C1-C6-alkyl groups, or R9 and R10 together form in which the are p and q are independently from one another selected from 0, 1 and 2, and R11 and R12 are independently selected from C1-C6-alkyl and phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy and phenyl, which is unsubstituted or substituted by one or two C1-C4-alkyl substituents, A is # , BCS233012 FC -21- in which the bond identified by "*" is bound directly to the phosphorus atom and in which the bond identified by "#" is bound directly to the oxazoline moiety, R14 are independently from one another selected from the group consisting of hydrogen, C1- C6-alkyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C7- cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R13 and R14 together with the carbon which they are bound to, form a C5-C6-cycloalkyl ring, R15 is selected from phenyl, benzyl, t-butyl, isopropyl, cyclohexyl, R16 is selected from hydrogen, methyl, ethyl, isopropyl, each R17 is independently selected from hydrogen, benzyl, methyl, ethyl, and each R18 is independently selected from cyclohexyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,6- dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl. R3 is preferably C1-C6-alkyl, C1-C6-haloalkyl, C3-C7-cycloalkyl or C6-C14-aryl, wherein the C6- C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl again is unsubstituted or substituted by one to five C1-C6-alkyl substituents. R3 is more preferably selected from the group consisting of 1-naphtyl, 2-naphtyl, 9-antracenyl, 9-phenantryl or phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-haloalkyl and phenyl, wherein the phenyl again is unsubstituted or substituted by one to five C1-C6- alkyl substituents. R3 is more preferably phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-tert- butylphenyl, 4-methoxyphenyl, 3,5-bis-tert-butyl-4-methoxyphenyl, 4-tert-butyl-2,6- dimethylphenyl, 4-fluorophenyl, 4-trifluoromehtylphenyl, 1-naphtyl, 9-antracenyl 2,4,6- triisopropylphenyl, 9-phenantryl or 2,6-diethyl-4-methylphenyl. BCS233012 FC -22- R4 and R5 are preferably independently from one another selected from the group consisting of hydrogen, C1-C6-alkyl, C6-C14-aryl, C1-C6-alkoxy or C1-C6-haloalkyl, wherein the C6-C14-aryl is unsubstituted or substituted by one to five C1-C4-alkyl substituents. R4 and R5 are more preferred independently from one another hydrogen or C1-C6-alkyl. More preferred R4 is hydrogen and R5 is hydrogen or methyl. R6 and R7 are preferably independently from one another selected from the group consisting of C1-C6- alkyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C6-C14-aryl, C6-C14-aryloxy and C6-C14-aryl-C1-C4-alkyl, piperidinyl and pyridyl, wherein the C1-C6-alkyl, C1-C6-alkoxy and di(C1-C6-alkyl)amino moieties are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl may be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl, C6-C14-aryloxy and C3-C12-cycloalkyl, as such or as part of a composite substituent, in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1-C6-alkyl substituents or R6 and R7 together with the phosphorus atom which they are bound to, form a phospholane ring, which may be substituted with one or two C1-C6-alkyl groups. R6 and R7 are more preferred independently from one another selected from the group consisting of ethyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl and benzyl. R6 and R7 are more preferred each the same and selected from the group consisting of ethyl, iso-propyl, tert-butyl, cyclopentyl, adamantyl and cyclohexyl. m is preferably 1. R8 is preferably C3-C6-alkyl, C3-C12-cycloalkyl, C6-C14-aryl or C6-C14-aryl-C1-C4-alkyl, BCS233012 FC -23- wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy. R8 is more preferred tert-butyl, iso-propyl or phenyl. R9 and R10 are preferably independently from one another selected from the group consisting of C1-C6- alkyl, C3-C12-cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl may be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, phenyl, C1-C4-alkoxy, C1-C4- haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R9 and R10 together with the phosphorus atom which they are bound to, form a phospholane ring, which may be substituted with one or two C1-C6-alkyl groups. R9 and R10 are more preferred each the same and 2-methylphenyl or 3,5-bismethylphenyl. A is preferably A1. R13 and R14 are preferably independently from one another selected from the group consisting of C1-C6- alkyl, C3-C12-cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R13 and R14 together with the carbon which they are bound to, form a C5-C6-cycloalkyl ring. R13 and R14 are more preferred each methyl. R15 is preferably phenyl or t-butyl, more preferred phenyl. R16 is preferably hydrogen or methyl, more preferred methyl. BCS233012 FC -24- Each R17 is preferably benzyl or methyl, more preferred benzyl. Each R18 is preferably cyclohexyl. Preferably, the chiral iridium hydride complexes according to the invention comprise a chiral chelating ligand of formula (IIa) or (IIb). Preferred are ligands of the formulae (IIa) and (IIb), wherein the substituents are defined as follows: R3 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C7-cycloalkyl or C6-C14-aryl, wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4- haloalkoxy and phenyl, wherein the phenyl again is unsubstituted or substituted by one to five C1-C6-alkyl substituents, R4 and R5 are independently from one another selected from the group consisting of hydrogen, C1-C6- alkyl, C1-C6-alkoxy, C6-C14-aryl or C1-C6-haloalkyl, wherein the C6-C14-aryl is unsubstituted or substituted by one to five C1-C4-alkyl substituents, R6 and R7 are independently from one another selected from the group consisting of C1-C6-alkyl, C1-C6- alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C6-C14-aryl, C6-C14-aryloxy and C6-C14- aryl-C1-C4-alkyl, piperidinyl and pyridyl, wherein the C1-C6-alkyl, C1-C6-alkoxy and di(C1-C6-alkyl)amino moieties are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl may be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryloxy, C3-C12-cycloalkyl and C6-C14-aryl, as such or as part of a composite substituent, in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1-C6-alkyl substituents or R6 and R7 together with the phosphorus atom which they are bound to, form a phospholane ring, which may be substituted with one or two C1-C6-alkyl groups, and BCS233012 FC -25- m is 1 or 2. More preferred are ligands of the formulae (IIa) and (IIb), wherein the substituents are defined as follows: R3 is selected from the group consisting of 1-naphtyl, 2-naphtyl, 9-antracenyl, 9-phenantryl or phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-haloalkyl and phenyl, wherein the phenyl again is unsubstituted or substituted by one to five C1-C6-alkyl substituents, R4 and R5 are independently from one another hydrogen or C1-C6-alkyl, R6 and R7 are independently from one another selected from the group consisting of ethyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, cyclohexyl, cyclopentyl, adamantyl and benzyl, and m is 1 or 2. Even more preferred are ligands of the formulae (IIa) and (IIb), wherein the substituents are defined as follows: R3 is selected from the group consisting of, phenyl, 2,6- or 3,5-dimethylphenyl, 2,4,6- trimethylphenyl, 4-tert-butylphenyl, 4-methoxyphenyl, 3,5-bis-tert-butyl-4-methoxyphenyl, 4-tert-butyl-2,6-dimethylphenyl, 4-fluorophenyl, 4-trifluoromethylphenyl, 1-naphtyl, 9- antracenyl 2,4,6-triisopropylphenyl, 9-phenantryl or 2,6-diethyl-4-methylphenyl, R4 is hydrogen, R5 is hydrogen or methyl, R6 and R7 are each the same and tert-butyl, cyclopentyl or cyclohexyl, and m is 1. Even more preferred are also ligands of the formulae (IIa) and (IIb), wherein the substituents are defined as follows: R3 is a group of formula BCS233012 FC -26- , wherein ** denotes the bond to the 6,7-dihydro-5H-cyclopenta[b]pyridine moiety, R19 is hydrogen, methyl or ethyl, and R20 is C1-C6-alkyl, R4 is hydrogen, R5 is C1-C4 alkyl or phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1- C4-alkoxy and C1-C4-haloalkoxy, R6 and R7 are independently from one another selected from the group consisting of C1-C6-alkyl, C3-C8- cycloalkyl, piperidinyl and pyridyl, and m is 1. Most preferred are ligands of the formulae (IIa) and (IIb), wherein the substituents are defined as follows: R3 is 2,6-diethyl-4-methylphenyl, R4 is hydrogen, R5 is methyl, R6 and R7 are each cyclohexyl, and m is 1. In another preferred embodiment, the chiral iridium hydride complexes according to the invention comprise a chiral chelating ligand of formula (IIIa) or (IIIb). Preferred ligands of formulae (IIIa) and (IIIb) are those, wherein the substituents are defined as follows: BCS233012 FC -27- A is A1 = , in which the bond identified by "*" is bound directly to the phosphorus atom and in which the bond identified by "#" is bound directly to the oxazoline moiety, R8 is C -C 3 6-alkyl, cycloalkyl, C6-C14-aryl or C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R13 and R14 are independently from one another selected from the group consisting of C1-C6-alkyl, C6- C14-aryl, C3-C12-cycloalkyl, and C6-C14-aryl-C1-C4-alkyl, wherein C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1- C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R13 and R14 together with the carbon which they are bound to, form a C5-C6-cycloalkyl ring, R9 and R10 are independently from one another selected from the group consisting of C1-C6-alkyl, C3- C12-cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl may be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, phenyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R9 and R10 together with the phosphorus atom which they are bound to, form a phospholane ring, which may be substituted with one or two C1-C6-alkyl groups. BCS233012 FC -28- More preferred ligands of formulae (IIIa) and (IIIb) are those, wherein the substituents are defined as follows: A is A1 = , in which the bond identified by "*" is bound directly to the phosphorus atom and in which the bond identified by "#" is bound directly to the oxazoline moiety, 8 R is iso-propyl, sec- iso-butyl, tert-butyl, phenyl or benzyl, R13 and R14 are independently from one another selected from the group consisting of C1-C6-alkyl, and C6-aryl-C1-C4-alkyl, wherein the C6-aryl in the C6-C14-aryl-C1-C4-alkyl moiety is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen and C1-C4-alkyl, R9 and R10 are independently from one another phenyl, 1-naphthyl or 2-naphthyl, which in each case is unsubstituted or substituted by one to five C1-C4-alkyl substituents. Most preferred ligands of formulae (IIIa) and (IIIb) are those, wherein the substituents are defined as follows: A is , in which the bond to the phosphorus atom and in which the bond identified by "#" is bound directly to the oxazoline moiety, 8 R is tert-butyl, R13 and R14 are each methyl, and BCS233012 FC -29- R9 and R10 are independently from one another phenyl, which is substituted by one or two methyl, in particular R9 and R10 are each the same and phenyl, which is substituted by one or two methyl or R9 and R10 are each the same and 2-methylphenyl or 3,5-dimethylphenyl. In another preferred embodiment, the chiral iridium hydride complexes according to the invention comprise a chiral chelating ligand of formula (IVa) or (IVb). Preferred ligands of formulae (IVa) and (IVb) are those, wherein the substituents are defined as follows: R15 is selected from phenyl, benzyl, t-butyl, isopropyl or cyclohexyl, R16 is selected from hydrogen, methyl, ethyl or isopropyl, R17 is selected from hydrogen, benzyl, methyl or ethyl, and R18 is selected from cyclohexyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,6-dimethylphenyl, 3,5-dimethylphenyl or 2,4,6-trimethylphenyl. More preferred ligands of formulae (IVa) and (IVb) are those, wherein the substituents are defined as follows: R15 is phenyl or t-butyl, R16 is hydrogen or methyl, R17 is benzyl or methyl, and R18 is cyclohexyl. Most preferred ligands of formulae (IVa) and (IVb) are those, wherein the substituents are defined as follows: R15 is phenyl, R16 is methyl, R17 is benzyl, and R18 is cyclohexyl. Preferably, the chiral iridium hydride complex is a complex of formula (V) [IrH(L*)(L(I))]Y, (V) BCS233012 FC -30- wherein L* is the chiral chelating ligand of formula (IIa), (IIb), (IIIa), (IIIb), (IVa) or (IVb), L(I) is the enone ligand of formula (I), and Y is a non-coordinating anion selected from the group consisting of [B(R21)4]-, PF6-, SbF6-, CF3SO3-, [Al{OC(CF3)3}4]− (VI) and ^-TRISPHAT (VII) CI (VI) (VII) wherein R21 is selected from fluorine and phenyl, which is unsubstituted or substituted with one to five substituents selected from C1-C4-alkyl, C1-C4-haloalkyl and halogen. Regarding L*, i.e. the chiral chelating ligand of formula (IIa), (IIb), (IIIa), (IIIb), (IVa) or (IVb), and L(I), i.e. the enone ligand of formula (I), the preferred, more preferred and most preferred definitions given above apply mutatis mutandis. Y is preferably a non-coordinating anion selected from the group consisting of [B(R21)4]-, PF6- and [Al{OC(CF3)3}4]− (VI) F3C CF3 F3C CF3 BCS233012 FC -31- (VI) wherein R21 is phenyl, which is unsubstituted or substituted with one to five substituents selected from C1-C4-alkyl, C1-C4-haloalkyl and halogen. Y is more preferred a non-coordinating anion selected from the group consisting of [B(R21)4]- and [Al{OC(CF3)3}4]− (VI) F3C CF3 F3C CF3 wherein R21 is with one to five substituents selected from fluorine and trifluoromethyl. Y is most preferred a non-coordinating anion selected from the group consisting of [B(R21)4]-, wherein R21 is 3,5-bis(trifluoromethyl)phenyl or 2,3,4,5,6-pentafluorophenyl. More preferred, the chiral iridium hydride complex is a complex of formula (V) [IrH(L*)(L(I))]Y, (V) wherein L* is the chiral chelating ligand of formula (IIa), (IIb), (IIIa), (IIIb), (IVa) or (IVb), BCS233012 FC -32- R3 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C7-cycloalkyl or C6-C14-aryl, wherein the C6-C14- aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl again is unsubstituted or substituted by one to five C1- C6-alkyl substituents; preferably 1-naphtyl, 2-naphtyl, 9-antracenyl, 9-phenantryl or phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-alkyl, C1-C4-haloalkyl and phenyl, wherein the phenyl again is unsubstituted or substituted by one to five C1-C6- alkyl substituents, R4 and R5 are independently from one another selected from the group consisting of hydrogen, C1-C6-alkyl, C6-C14-aryl, C1-C6-alkoxy or C1-C6-haloalkyl, wherein the C6- C14-aryl is unsubstituted or substituted by one to five C1-C4-alkyl substituents; preferably are independently from one another hydrogen or C1-C6-alkyl, BCS233012 FC -33- R6 and R7 are independently from one another selected from the group consisting of C1-C6- alkyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C6-C14-aryl, C6-C14- aryloxy and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl, C1-C6-alkoxy and di(C1-C6-alkyl)amino moieties are optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl may be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4- haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl, C6-C14-aryloxy and C3-C12-cycloalkyl, as such or as part of a composite substituent, in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4- haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1-C6-alkyl substituents or R6 and R7 together with the phosphorus atom which they are bound to, form a phospholane ring, which may be substituted with one or two C1-C6-alkyl groups, m is 1, R8 is C3-C6-alkyl, C3-C12-cycloalkyl, C6-C14-aryl or C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4- haloalkoxy, R9 and R10 are independently from one another selected from the group consisting of C1-C6- alkyl, C3-C12-cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl is optionally substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4- haloalkoxy and phenyl, wherein the phenyl may be substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, phenyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and BCS233012 FC -34- wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4- haloalkoxy, or R9 and R10 together with the phosphorus atom which they are bound to, form a phospholane ring, which may be substituted with one or two C1-C6-alkyl groups, A is A1 = , wherein the bond identified by "*" is bound directly to the phosphorus atom and in which the bond identified by "#" is bound directly to the oxazoline moiety, 1 R 3 and R14 are preferably from one another selected from the group consisting of C1-C6-alkyl, C3-C12-cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4- haloalkoxy, or R13 and R14 together with the carbon which they are bound to, form a C5-C6-cycloalkyl ring, R15 is phenyl or t-butyl, preferably phenyl, R16 is hydrogen or methyl, preferably methyl, each R17 is benzyl or methyl, preferably benzyl, and each R18 is cyclohexyl, L(I) is the enone ligand of formula (I), BCS233012 FC -35- i 0 , wherein R1 is selected from the group consisting of C1-C500-alkyl, C2-C500-alkenyl, C6-C14-aryl, wherein C1-C500-alkyl and C2-C500-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500- haloalkyl, and C1-C500-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, R1a is selected from the group consisting of hydrogen, C1-C4-alkylcarbonyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a C5-C7-cycloalkanone ring, preferably a cyclohexanone ring, wherein the C5-C7-cycloalkanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C6-alkyl, and C1-C6-alkoxy, R2 is selected from the group consisting of C1-C500-alkyl, C6-C14-aryl, wherein C1-C500-alkyl is unsubstituted or substituted by substituent(s) independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500- haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and BCS233012 FC -36- wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1- C500-alkoxy and C1-C500-haloalkoxy, and the arrow indicates a bond to the iridium atom, and Y is a non-coordinating anion selected from the group consisting of [B(R21)4]-, PF6-, SbF6-, CF3SO3-, [Al{OC(CF3)3}4]− (VI) and ^-TRISPHAT (VII) CI F3C (VI) (VII) wherein R21 is selected from fluorine and phenyl, which is unsubstituted or substituted with one to five substituents selected from C1-C4-alkyl, C1-C4-haloalkyl and halogen, preferably is a non-coordinating anion selected from the group consisting of [B(R21)4]- and [Al{OC(CF3)3}4]− (VI) F3C CF3 F3C CF3 BCS233012 FC -37- wherein R21 is phenyl, which is unsubstituted or substituted with one to five substituents selected from fluorine and trifluoromethyl. More preferred, the chiral iridium hydride complex is a complex of formula (V) [IrH(L*)(L(I))]Y, (V) wherein L* is the chiral chelating ligand of formula (IIa) or (IIb), 6 R 6 R m wherein R3 is a group of formula , wherein ** denotes the bond to the 6,7-dihydro-5H-cyclopenta[b]pyridine moiety, R19 is hydrogen, methyl or ethyl, preferably ethyl, and R20 is C1-C6-alkyl, preferably methyl, R4 is hydrogen, BCS233012 FC -38- R5 is C1-C4 alkyl or phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4- haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, preferably methyl, R6 and R7 are independently from one another selected from the group consisting of C1-C6- alkyl, C3-C8-cycloalkyl, piperidinyl and pyridyl, preferably cyclohexyl, and m is 1, L(I) is the enone ligand of formula (I), o , wherein R1 is selected from the group consisting of methyl, vinyl and phenyl, wherein the vinyl is substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one, two or three substituents selected independently from each other from methyl, ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), methoxy, ethoxy, propoxy, and 1-methylethoxy, preferably from methyl and methoxy, more preferably from methoxy, and wherein in case R1 is phenyl, this phenyl is unsubstituted. R1a is selected from the group consisting of hydrogen, C1-C4-alkylcarbonyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a C5-C7-cycloalkanone ring, preferably a cyclohexanone ring, wherein the C5-C7-cycloalkanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or BCS233012 FC -39- substituted by one to five substituents selected independently from each other from halogen, C1-C6-alkyl, and C1-C6-alkoxy, R2 is phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl, C1-C100-alkoxy and C1-C100-haloalkoxy, and the arrow indicates a bond to the iridium atom, and Y is a non-coordinating anion selected from the group consisting of [B(R21)4]-, PF6-, SbF6-, CF3SO3-, [Al{OC(CF3)3}4]− (VI) and ^-TRISPHAT (VII) (VI) (VII) wherein R21 is selected from fluorine and phenyl, which is unsubstituted or substituted with one to five substituents selected from C1-C4-alkyl, C1-C4-haloalkyl and halogen, preferably is a non-coordinating anion selected from the group consisting of [B(R21)4]- and [Al{OC(CF3)3}4]− (VI) BCS233012 FC -40- F3C CF3 wherein R21 is with one to five substituents selected from fluorine and trifluoromethyl. More preferred, the chiral iridium hydride complex is a complex of formula (V) [IrH(L*)(L(I))]Y, (V) wherein L* is the chiral chelating ligand of formula (IIa) or (IIb), wherein R3 is 2,6-diethyl-4-methylphenyl, R4 is hydrogen, R5 is methyl, R6 and R7 are each cyclohexyl, and m is 1, L(I) is the enone ligand of formula (I), wherein R1 is methyl, phenyl, styryl or 4-methoxystyryl (para-methoxystyryl), BCS233012 FC -41- R1a is hydrogen or acetyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, and R2 is phenyl or 4-methoxyphenyl, and Y is a non-coordinating anion selected from the group consisting of [Al{OC(CF3)3}4]− of formula (VI) and [B(R21)4]-, wherein R21 is 3,5-bis(trifluoromethyl)phenyl or 2,3,4,5,6-pentafluorophenyl. More preferred, the chiral iridium hydride complex is a complex of formula (V) [IrH(L*)(L(I))]Y, (V) wherein L* is the chiral chelating ligand of formula (IIa) or (IIb), wherein R3 is 2,6-diethyl-4-methylphenyl, R4 is hydrogen, R5 is methyl, R6 and R7 are each cyclohexyl, and m is 1, L(I) is the enone ligand of formula (I-H), wherein R1 is methyl or styryl, and BCS233012 FC -42- R2 is phenyl, and Y is a non-coordinating anion selected from the group consisting of [Al{OC(CF3)3}4]− of formula (VI) and [B(R21)4]-, wherein R21 is 3,5-bis(trifluoromethyl)phenyl or 2,3,4,5,6-pentafluorophenyl. Most preferred, the chiral iridium hydride complex is a complex of formula (VIII), - (VIII), wherein R1’ is methyl, phenyl or styryl, and [Y]- is the non-coordinating anion [B(R21)4]-, wherein R21 is 3,5-bis(trifluoromethyl)phenyl or 2,3,4,5,6-pentafluorophenyl. The chiral iridium hydride complexes according to the invention can be prepared for example from a chiral iridium catalyst known from WO 2019/185541, WO 2021/058457 and WO 2021/058458 by hydrogenation and subsequent reaction with the desired enone compound, e.g. simply from a spent catalyst resulting from the hydrogenation reaction disclosed in WO 2019/185541, WO 2021/058457 and WO 2021/058458 using a chiral iridium catalyst as shown in scheme 2: Scheme 2: BCS233012 FC -43- [Y]- [Y] - R1, R2 and [Y]- are defined as specified above, and represents the chiral (P,N)-ligand. The cyclooctadiene stabilized chiral iridium catalysts depicted in scheme 2, their preparation and their use in hydrogenation reactions is known from WO 2019/185541, WO 2021/058457 and WO 2021/058458. Using said catalysts in a hydrogenation process, preferably the hydrogenation process disclosed in WO 2019/185541, WO 2021/058457 and WO 2021/058458, yields a spent catalyst that can be converted to a chiral iridium hydride complex according to the invention by reacting the spent catalyst with the desired enone of formula (I-a). The chiral (P,N)-ligand remains unchanged. The chiral iridium hydride complexes according to the invention can also be prepared from a spent catalyst resulting from the hydrogenation reaction disclosed herein using an chiral iridium hydride complex according to the invention, by reacting the spent catalyst with the desired enone of formula (I-a). Analogously to the procedure shown in scheme 2, in the first step, i.e. the hydrogenation reaction, a spent catalyst is formed, that in a further step is reacted with the desired enone of formula (I-a). Preferably, reaction of the spent catalyst with enone of formula (I-a) is conducted in the presence of an solvent. Suitable solvents are for example halogenated alcohols such as 2,2,2,-trifluoroethanol, hexafluoroisopropanol (1,1,1,3,3,3-hexafluoro-2-propanol) and tetrafluoropropanol (2,2,3,3-tetrafluoro-1-propanol), halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such BCS233012 FC -44- as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane and anisole, and esters such as ethyl acetate, isopropyl acetate, and mixtures thereof. Preferred solvents are selected from the group consisting of 2,2,2,-trifluoroethanol, hexafluoroisopropanol, 1,2-dichloroethane, tetrafluoropropanol, 1,4-dioxane, isopropyl acetate, toluene, and mixtures thereof. More preferred solvents are selected from the group consisting of 2,2,2,-trifluoroethanol, hexafluoroisopropanol, 1,2-dichloroethane, tetrafluoropropanol, and mixtures thereof. Especially preferred are 2,2,2,-trifluoroethanol and hexafluoroisopropanol. Most preferred is hexafluoroisopropanol, i.e.1,1,1,3,3,3-hexafluoro-2-propanol. Preferably, in the reaction of the spent catalyst with enone of formula (I-a) and in the hydrogenation reaction the same solvent is used. Preferably, reaction of the spent catalyst with enone of formula (I-a) is conducted at a temperature within the range of from 10 °C to 130 °C, more preferably 20 °C to 80 °C. The invention further relates to a process for preparing optically active 4-substituted 1,2,3,4- tetrahydroquinolines by enantioselective hydrogenation of the corresponding 4-substituted 1,2- dihydroquinolines in presence of a chiral iridium hydride complex according to the invention. The invention relates in particular to a process for preparing a compound of formula (IXa) or (IXb), 25 25 (R26 OR (R26)n O R wherein R22 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C3- C6-cycloalkyl, C6-C14-aryl, or C6-C14-aryl-C1-C4-alkyl, BCS233012 FC -45- wherein the C1-C6-alkyl, C3-C6-cycloalkyl and the C1-C6-alkoxy in the C1-C6-alkoxy-C1-C6-alkyl moiety, are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R23 and R24 are the same and are selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6- haloalkyl and C1-C6-alkoxy-C1-C6-alkyl, or R23 and R24 together with the carbon which they are bound to, form a C3-C6-cycloalkyl ring, R25 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylamino, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4-alkyl, C2-C6-alkenyloxy, 9- flurorenylmethyleneoxy, C6-C14-aryl, C6-C14-aryloxy, C6-C14-aryl-C1-C4-alkyloxy or C6-C14-aryl- C1-C4-alkyl, wherein the C6-C14-aryl as such or as part of a composite substituent is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4- haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, n is 0, 1, 2, 3 or 4, and each substituent R26, if present, is independently selected from the group consisting of halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, hydroxyl, amino and –C(=O)-C1-C6-alkyl, comprising enantioselective hydrogenation of a compound of formula (X) (R26)n BCS233012 FC -46- (X) wherein the substituents R22, R23, R24, R25, R26 and the integer n are each as defined for the compound of the formula (IXa) or (IXb), characterized in that the process is conducted in presence of a chiral iridium hydride complex according to the invention. Preferably, compounds of the formula (IXa) or (IXb), in particular (IXa), are those, wherein the substituents are defined as follows: R22 is C1-C6-alkyl or C6-C14-aryl-C1-C4-alkyl, wherein C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R23 and R24 are the same and are selected from C1-C4-alkyl, R25 is C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, phenyl or benzyl, n is 0, 1 or 2, and each substituent R26, if present, is independently selected from the group consisting of halogen, C1-C6-alkyl and C1-C6-haloalkyl. More preferred compounds of the formula (IXa) or (IXb), in particular (IXa), are those, wherein the substituents are defined as follows: R22 is C1-C6-alkyl, R23 and R24 are the same and are selected from C1-C4-alkyl, R25 is C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, phenyl or benzyl, n is 0, 1 or 2, and each substituent R26, if present, is independently selected from the group consisting of halogen, C1-C6-alkyl and C1-C6-haloalkyl. BCS233012 FC -47- Even more preferred compounds of the formula (IXa) or (IXb), in particular (IXa), are those, wherein the substituents are defined as follows: R22 is C1-C4-alkyl, R23 and R24 are each methyl, R25 is C1-C4-alkyl, n is 0 or 1, and R26, if present, is fluorine. Even more preferred compounds of the formula (IXa) or (IXb), in particular (IXa), are those, wherein the substituents are defined as follows: R22 is methyl, ethyl or n-propyl, R23 and R24 are each methyl, R25 is C1-C4-alkyl, n is 0 or 1, R26, if present, is fluorine. Even more preferred compounds of the formula (IXa) or (IXb), in particular (IXa), are those, wherein the substituents are defined as follows: R22 is methyl or n-propyl, R23 and R24 are each methyl, R25 is methyl, n is 0 or 1, and R26, if present, is fluorine. Most preferred compounds of the formula (IXa) or (IXb), in particular (IXa), are those, wherein the substituents are defined as follows: BCS233012 FC -48- R22 is methyl, R23 and R24 are each methyl, R25 is methyl, and n is 0. The process according to the invention comprises enantioselective hydrogenation of a compound of formula (X). The substituents R22, R23, R24, R25, R26 and the integer n in the compound of formula (X) are each as defined for the compound of the formula (IXa) or (IXb). Preferred, particular preferred, more preferred, even more preferred and most preferred meanings of the substituents R22, R23, R24, R25, R26 and the integer n as outlined above for the compound of the formula (IXa) or (IXb) apply mutatis mutandis for compound of formula (X). The amount of chiral iridium hydride complex used is preferably within the range of from 0.001 mol% to 5 mol%, more preferably 0.001 mol% to 4 mol%, even more preferably 0.002 mol% to 3 mol%, most preferably 0.005 mol% to 1.0 mol%, based on the amount of the compound of formula (X). Preferably, the hydrogenation is conducted using hydrogen gas at a pressure of from 1 to 300 bar, preferably 3 to 200 bar, most preferably 20 to 150 bar. The hydrogenation is preferably conducted at a temperature within the range of from 20 °C to 130 °C, more preferably 30 °C to 100 °C. The process according to the invention is preferably conducted in the presence of a solvent. Suitable solvents are halogenated alcohols such as 2,2,2,-trifluoroethanol, hexafluoroisopropanol (1,1,1,3,3,3- hexafluoro-2-propanol) and tetrafluoropropanol (2,2,3,3-tetrafluoro-1-propanol), halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, dichloroethane and trichloroethane, aromatic hydrocarbons such as benzene, toluene and xylene, ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2- dimethoxyethane, 1,2-diethoxyethane and anisole, and esters such as ethyl acetate, isopropyl acetate, and mixtures thereof. Preferred solvents are selected from the group consisting of 2,2,2,-trifluoroethanol, hexafluoroisopropanol, 1,2-dichloroethane, tetrafluoropropanol, 1,4-dioxane, isopropyl acetate, toluene, and mixtures thereof. BCS233012 FC -49- More preferred solvents are selected from the group consisting of 2,2,2,-trifluoroethanol, hexafluoroisopropanol, 1,2-dichloroethane, tetrafluoropropanol, and mixtures thereof. Especially preferred are 2,2,2,-trifluoroethanol and hexafluoroisopropanol. Most preferred is hexafluoroisopropanol, i.e.1,1,1,3,3,3-hexafluoro-2-propanol. The amount of solvent, if present, is preferably within the range of from 0.5 to 20 mass equivalents, more preferably 1 to 10 mass equivalents, most preferably 2 to 7 mass equivalents, in particular 4 to 6 mass equivalents, based on the amount of the compound of the formula (X). The process according to the invention is preferably conducted in the presence of an additive, which is selected from the group consisting of Brønsted acids and Lewis acids. The additive is preferably selected from the group consisting of hexafluorophosphoric acid, acetic acid, tri- fluoromethylsulfonic acid, water, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid, tetrafluoroboric acid diethylether complex, nafion, amberlyst, 1,1,1,3,3,3-hexafluoro-2-(trifluoro- methyl)propan-2-ol, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluoro- phenyl)borane, borane tetrahydrofurane complex, boric acid, aluminum (III) trifluoromethanesulfonate, zinc (II) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethyl aluminum, boron trifluoride, complexes of boron trifluoride, and mixtures thereof. Suitable complexes of boron trifluoride are complexes of boron trifluoride with organic solvents, such as dialkyl ethers or alcohols, and complexes of boron trifluoride with organic acids, such as carboxylic acids. Preferred boron trifluoride complexes are selected from the group consisting of boron trifluoride-diethylether complex, boron trifluoride acetic acid complex and boron trifluoride n-propanol complex. More preferred, the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, tetrafluoroboric acid diethylether complex, triphenylborane, tris[3,5-bis(trifluoromethyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethyl aluminum, boron trifluoride, complexes of boron trifluoride, and mixtures thereof, wherein the complexes of boron trifluoride are preferably selected from the group consisting of boron trifluoride-diethylether complex, boron trifluoride acetic acid complex and boron trifluoride n- propanol complex. BCS233012 FC -50- Even more preferred, the additive is selected from the group consisting of hexafluorophosphoric acid, pentafluorophenol, 3,5-bis(trifluoromethyl)phenol, triphenylborane, tris[3,5-bis(trifluoro- methyl)phenyl]borane, tris(2,3,4,5,6-pentafluorophenyl)borane, aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, aluminum (III) fluoride, titanium (IV) isopropoxide, trimethyl aluminum, boron trifluoride, complexes of boron trifluoride, and mixtures thereof, wherein the complexes of boron trifluoride are preferably selected from the group consisting of boron trifluoride-diethylether complex, boron trifluoride acetic acid complex and boron trifluoride n-propanol complex. Most preferred, the additive is selected from the group consisting of aluminum (III) trifluoromethanesulfonate, scandium (III) trifluoromethanesulfonate, tris(2,3,4,5,6-pentafluorophenyl)borane, hexafluorophosphoric acid, boron trifluoride and complexes of boron trifluoride, wherein the complexes of boron trifluoride are preferably selected from the group consisting of boron trifluoride diethylether complex, boron trifluoride acetic acid complex and boron trifluoride n-propanol complex. If present, the amount of additive selected from the group consisting of Brønsted acids and Lewis acids used is preferably within the range of from 0.1 mol% to 10 mol%, more preferably 0.2 mol% to 5 mol%, most preferably 0.3 mol% to 2 mol%, in particular 0.4 mol% to 1 mol%, based on the amount of the compound of the formula (X). Abbreviations and Acronyms: a/a By area BDA Benzylideneacetone calcd. Calculated Dba Dibenzylideneacetone Et Ethyl EtOAc Ethylacetate EtOH Ethanol GC Gas chromatography h Hour(s) HFIP 1,1,1,3,3,3-hexafluoro-2-propanol HPLC High performance liquid chromatography BCS233012 FC -51- HRMS High resolution mass spectrometry Me Methyl min Minute(s) NMR Nuclear magnetic resonance spectroscopy r.t. Room temperature TMQA 1-(2,2,4-trimethylquinolin-1(2H)-yl)ethan-1-one w/w By weight
BCS233012 FC -52- Examples Preparation of Chiral Iridium Hydride Complexes : Chiral iridium hydride complexes of formula (VIII) have been prepared from the respective spent catalyst resulting from the hydrogenation process known from WO 2021/058458 as shown in scheme 3: Scheme 3: + ÷ - - [Y] [Y] 7 wherein R1’ is methyl, phenyl or styryl, and [Y]- is tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Catalyst (XI) and preparation thereof is known from WO 2021/058458. Chiral iridium hydride complexes of formulae (XII), (XIII), and (XIV) have been prepared analogously. Example 1: 255 mg catalyst (XI) (0.154 mmol) were dissolved in dry 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) (30 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 50 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 1.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing benzylideneacetone (BDA) (115 mg, 0.779 mmol) in HFIP (1.0 ml). BCS233012 FC -53- The reaction mixture was stirred at 50 °C. After 2 h a yellow precipitate formed and separated from the solution. Further stirring at 50 °C resulted in formation of additional voluminous yellow precipitate. After 22 h the mixture was allowed to reach r.t. and the precipitate was separated by filtration and washed with HFIP (2 x 2 ml) and n-Pentan (3 x 2 ml) to give the yellow crystalline air stable chiral iridium hydride complex of formula (VIII-1) (207 mg, 79% Yield), the structure of which was confirmed by 2D NMR studies, high resolution mass spectroscopy and X-ray crystallography. (VIII-1) 1H-NMR (400.13 MHz, CD2Cl2): Cation, δ = -22.02 (d, 1H, J = 23.5 Hz, Ir-H), 0.55 (qt, 1H, J = 13.1, 3.6 Hz, Cy-CH2), 0.68–0.77 (m, 1H, Cy-CH2) 0.92–1.17 (m, 7H, Cy-CH2), 1.02 (t, 3H, J = 8.4 Hz, 2’-CH3-Et), 1.13 (t, 3H, J = 8.4 Hz, 6’-CH3-Et), 1.20–1.41 (m, 3H, Cy-CH, Cy-CH2), 1.52–1.80 (m, 9H, Cy-CH2), 2.10– 2.22 (m, 1H, H-6a), 2.17 (s, 3H, 4’-CH3), 2.25–2.35 (m, 2H, 6’-CH2a-Et, Cy-CH), 2.37–2.47 (m, 1H, 6’-CH2b- Et), 2.42 (s, 3H, 3-CH3), 2.44 (s, 3H, 1’’-CH3), 2.55 (dq, 1H, J = 13.7, 7.4 Hz, 2’-CH2a-Et), 2.74–2.85 (m, 2H, H-5a, H-6b), 2.96–3.03 (m, 1H, H-5b), 3.08 (dt, 1H, J = 14.1, 7.5 Hz, 2’-CH2b-Et), 5.41 (t, 1H, J = 8.4 Hz, H- 7), 6.71 (s, 1H, H-3’’), 6.80 (s, 1H, H-3’), 7.0 (s, 1H, H-5’), 7.14 (s, 1H, H-2), 7.32 (m, 5H, Ar-Benzacet); Anion, δ = 7.56 (br s, 4H, H-4), 7.72 (t, 8H, J = 2.6 Hz, H-2, H-6). 13C-NMR (100.61 MHz, CD2Cl2): Cation δ = 27.2 (d, J = 6.3 Hz), 26.8 (d, J = 5.8 Hz), 26.7, 26.6, 26.5, 26.3, 26.2, 25.9, 25.6 (Cy-CH2), 15.1 (6’-CH3-Et), 18.3 (2’-CH3-Et), 19.2 (3-CH3), 21.3 (4’-CH3), 24.6 (C-5), 27.3 (1’’-CH3), 27.6 (6’-CH2-Et), 30.1 (2’-CH2-Et), 32.8 (d, J = 7.5 Hz, C-6), 39.7 (d, J = 35.7 Hz, Cy-CH), 42.5 (d, J = 35.7 Hz, Cy-CH), 79.1 (d, J = 8.2 Hz, C-7), 122.6 (C- 1’), 127.7 (C-6’’, C-10’’), 128.2 (C-2), 128.2 BCS233012 FC -54- (C-5’), 128.7 (C-7’’, C-9’’), 129.3 (C-3’), 130.1 (C-8’’), 136.0 (C-3’’), 137.2 (C-3), 140.8 (C-2’), 143.3 (C- 4’), 146.0 (C-5’’), 147.9 (C-4’’), 148.6 (C-4), 153.5 (d, J = 3.3 Hz, C-8), 155.5 (C-1), 213.3 (C=O); Anion, δ = 117.8 (m, C-4), 125.0 (q, J = 272 Hz, 3-CF3 ,5-CF3), 129.3 (qq, J = 2.68, Hz, 31.4 Hz, C-3, C-5), 135.2 (br, C-2, C-6), 162.2 (q, 1J13C,11B = 49.7 Hz, C-1ipso). 11B-NMR (128.38 MHz, CD2Cl2): δ = ‒ 6.6 19F-NMR (376.46 MHz, CD2Cl2): δ = ‒ 62.92 31P{1H}-NMR (161.99 MHz, CD2Cl2): δ = 113.61 (m) HRMS (ESI-TOF+) m/z calcd. for C42H56NO2PIr [M]+ 830.3378, found 830.3669 HRMS (ESI-TOF-) m/z calcd. for C32H12BF24 [M]- 863.0648, found 863.0667 Diastereomer of iridium hydride (VIII-1) 1H-NMR (400.13 MHz, CD2Cl2): Cation, δ = -21.8 (d, 1H, J = 23.9 Hz, Ir-H), 0.34 (m, 1H), 0.64–0.72 (m, 1H), 0.66 (t, 3H, J = 7.4 Hz, CH3), 0.91–1.15 (m, 9H), 1.30 (t, 3H, J = 7.6 Hz, CH3), 1.28–1.46 (m, 6H), 1.51– 1.68 (m, 5H), 1.98–2.22 (m, 3H), 2.26 (s, 3H, CH3), 2.38 (s, 3H, CH3), 2.44 (s, 3H, CH3), 2.72 (q, 2H, J = 7.5 Hz), 2.80–2.88 (m, 2H), 2.97–3.13 (m, 2H), 5.17 (t, 1H, J = 8.3 Hz), 6.71 (s, 1H), 6.91 (s, 1H), 7.24 (s, 1H), 7.36–7.38 (m, 4H), 7.5 (m, 1H); Anion, δ = 7.56 (br s, 4H, H-4), 7.73 (m, 8H, H-2, H-6). 31P{1H}-NMR (161.99 MHz, CD2Cl2): δ = 111.33 (d, J = 21.1 Hz) Example 2: Catalyst (XI) has been used in a hydrogenation process as disclosed in WO 2021/058458 to hydrogenate 1- (2,2,4-trimethylquinolin-1(2H)-yl)ethan-1-one (TMQA). A solution of TMQA (585 mg, 2.72 mmol) in HFIP (2.7 ml) was added to a Schlenk-tube containing catalyst (XI) (46 mg, 27.8 μmol) under argon. The resulting yellow suspension was subjected to ultrasound-bath at r.t. for some minutes until a turbid solution was obtained. The mixture was transferred to an H.E.L autoclave 20 mL under argon. The autoclave was purged 5 times with 1.0 MPa H2 and then pressurized with H2 to 6.0 MPa. The hydrogenation was continued compensating the gas uptake with H2. After 25 min at r.t. the pressure was released, and the autoclave was purged 5 times with 0.6 MPa argon. The yellow clear solution was transferred to a Schlenk-tube containing 5 molar equivalents of BDA (0.47 M in HFIP, 0.3 ml) under argon and the reaction mixture was stirred 21 h at 50 °C yielding hydride complex of formula (VIII-1) quantitatively according with 31P quant.-NMR. BCS233012 FC -55- 7 + [Y] - (VIII-1) wherein [Y]- is tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Example 3: Catalyst (XI) has been used in a hydrogenation process as disclosed in WO 2021/058458 to hydrogenate 1- (2,2,4-trimethylquinolin-1(2H)-yl)ethan-1-one. 62 mg catalyst (XI) (37.5 μmol) were dissolved in dry HFIP (7.5 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 25 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 1.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing dibenzylideneacetone (Dba) (43.9 mg, 0.187 mmol) in HFIP (1.0 ml). 0 The reaction mixture was stirred at 50 °C. After 22 h the resulted dark red solution was allowed to get r.t. yielding quantitatively a mixture of two diastereomeric iridium hydride complexes (1:1) of formula (VIII-2). Products characterized in solution by NMR. BCS233012 FC -56- [Y]- (VIII-2) wherein [Y]- is tetrakis[3,5-bis(trifluoromethyl)phenyl]-borate. 31P{1H}-NMR (161.99 MHz, HFIP): δ = 111.95 (d, J = 20.3 Hz), 113.79 (m) Example 4: 255 mg catalyst (XI) (154 μmol) were dissolved in dry HFIP (30 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 50 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 2.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing 98% dibenzylideneacetone (Dba) (184.8 mg, 0.773 mmol). 0 The reaction mixture was stirred at 50 °C. After 44 h the resulted dark red solution was allowed to get r.t. and the solvent was removed in vacuum. The residue was washed with n-pentane (2 x 10 ml), n- pentane/dichloromethane (40:1, 2 x 10 ml), n-pentane/dichloromethane (20:1, 2 x 10 ml) and n- pentane/dichloromethane (10:1, 1 x 10 m5). Drying in high vacuum gave a dark orange solid (208.8 mg, 76% yield) consisting of a mixture of two diastereomeric iridium hydride complexes (1:0.9) of formula (VIII-2). BCS233012 FC -57- + [Y]- (VIII-2) wherein [Y]- is tetrakis[3,5-bis(trifluoromethyl)phenyl]-borate. 1H-NMR (400.13 MHz, CD2Cl2, 2 diastereomers): Cation, δ = -21.37 (br s, Ir-H), -21.17 (d, J = 23.7 Hz, Ir- H), 0.38 (q, J = 13.1 Hz, 1H), 0.69 (t, J = 7.4 Hz, 3H), 0.72 – 1.26 (m, 24H), 1.29 (t, J = 7.6 Hz, 6H), 1.32 – 1.74 (m, 20H), 1.98 – 2.13 (m, 5H), 2.19 (s, 3H), 2.21– 2.41 (m, 5H), 2.43 (s, 3H), 2.45 (s, 3H), 2.56 – 2.67 (m, 1H), 2.69 – 2.93 (m, 6H), 2.98 – 3.13 (m, 4H), 5.24 (t, J = 8.3 Hz, 1H), 5.63 (br s, 1H), 6.87 (s, 1H), 6.91 (s, 1H), 7.00 (d, J = 16.1 Hz, 1H), 7.00 (s, 1H), 7.10 (s, 2H), 7.15 (s, 2H), 7.35 – 7.45 (m, 10H), 7.46 – 7.51 (m, 5H), 7.60 – 7.71 (m, 8H), 7.92 (d, J = 16.1 Hz, 1H); Anion, δ = 7.58 (br s, 8H), 7.75 (dt, J = 5.1 Hz, 16H). 13C-NMR (100.61 MHz, CD2Cl2, 2 diastereomers): Cation, δ = 14.93, 19.09, 19.23, 20.59, 21.15, 21.35, 24.52 (d, J = 2.6 Hz), 24.63, 24.77, 25.97, 26.03, 26.13, 26.20, 26.24, 26.34, 26.48, 26.60 (d, J = 2.9 Hz), 26.68, 26.73, 26.81, 26.86, 26.91, 26.96, 27.28, 28.58 (d, J = 3.1 Hz), 32.12, 32.21, 39.17 (d, J = 49.6 Hz), 40.00 (d, J = 52.2 Hz), 42.02 (d, J = 44.2 Hz), 81.79 (br s), 124.27, 124.46, 128.15, 128.23, 128.50 (br s), 128.86, 128.95, 129.08, 129.16, 129.42, 129.59 (d, J = 3.3 Hz), 130.15, 131.39 (br s), 131.91 (d, J = 3.1 Hz), 132.25, 132.42, 134.79 (d, J = 13.5 Hz), 135.70, 136.70, 137.44 (br s), 141.15, 141.33, 141.47, 143.94, 145.89, 146.39, 148.35, 148.70 (d, J = 11.2 Hz), 200.10, 201.99; Anion, δ = 117.84 (p, J = 4.0 Hz, C-4), 125.00 (q, J = 272.3 Hz, 3-CF3 ,5-CF3), 129.29 (qq, J = 2.9, Hz, 30.6 Hz, C-3, C-5), 135.20 (br, C-2, C-6), 162.16 (q, 1J13C,11B = 49.8 Hz, C-1ipso). 11B-NMR (128.38 MHz, CD2Cl2): δ = ‒ 6.56 19F-NMR (376.46 MHz, CD2Cl2): δ = ‒ 62.83 31P{1H}-NMR (161.99 MHz, CD2Cl2, 2 diastereomers): δ = 111.85 (d, J = 20.6 Hz), 114.19 (m) HRMS (ESI-TOF+) m/z calcd. for C42H56NO2PIr [M]+ 918.3991, found 918.4016 HRMS (ESI-TOF-) m/z calcd. for C32H12BF24 [M]- 863.0659, found 863.0665 BCS233012 FC -58- Example 5: 255 mg catalyst (XI) (154 μmol) were dissolved in dry HFIP (30 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 50 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 2.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing 97% trans-Chalcone (165.7 mg, 0.772 mmol). The reaction mixture was stirred at solution was allowed to get r.t. and the solvent was removed in vacuum. The residue was washed with n-pentane (3 x 10 ml), n- pentane/dichloromethane (40:1, 3 x 10 ml) and n-pentane (1 x 10 ml). Drying in high vacuum gave an orange crystalline solid (216.3 mg, 80% yield) consisting of a mixture of two diastereomeric iridium hydride complexes (1:0.92) of formula (VIII-3). (V111-3) wherein [Y]- is tetrakis[3,5-bis(trifluoromethyl)phenyl]-borate. BCS233012 FC -59- 1H-NMR (400.13 MHz, CD2Cl2, 2 diastereomers): Cation, δ = -21.30 (d, J = 23.3 Hz, Ir-H), -21.11 (d, J = 23.7 Hz, Ir-H), 0.40 (qt, J = 12.9, 3.4 Hz, 1H), 0.50 – 0.66 (m, 3H), 0.67 (t, J = 7.5 Hz, 3H), 0.70 – 0.81 (m, 2H), 0.82 – 0.94 (m, 3H), 0.89 (t, J = 7.2 Hz, 3H), 0.96 – 1.14 (m, 8H), 1.01 (t, J = 7.6 Hz, 3H), 1.08 (t, J = 7.6 Hz, 3H), 1.19 – 1.53 (m, 14H), 1.53 – 1.69 (m, 10H), 1.90 (t, J = 10.4 Hz, 1H), 2.04 (m, 1H), 2.11 (s, 3H), 2.14 (s, 3H), 2.16 – 2.41 (m, 6H), 2.42 (s, 3H), 2.45 (s, 3H), 2.55 (ddq, J = 26.6, 15.2, 7.5 Hz, 2H), 2.74 (dq, J = 15.1, 7.8 Hz, 1H), 2.80 – 2.94 (m, 4H), 2.95 – 3.06 (m, 2H), 3.11 (dddd, J = 13.3, 10.2, 6.5, 3.1 Hz, 2H), 5.24 (t, J = 8.2 Hz, 1H), 5.53 (t, J = 8.2 Hz, 1H), 6.53 (s, 1H), 6.56 (s, 1H), 6.81 (s, 1H), 6.92 (s, 1H), 7.15 (s, 1H), 7.34 – 7.40 (m, 4H), 7.40 – 7.46 (m, 7H), 7.52 – 7.60 (m, 4H), 7.61 – 7.65 (m, 2H), 7.68 (dddd, J = 9.2, 6.7, 3.1, 1.8 Hz, 2H), 7.95 – 8.03 (m, 2H), 8.04 – 8.14 (m, 2H); Anion, δ = 7.57 (br s, 8H, H-4), 7.74 (dt, 16H, J = 5.1, 2.2 Hz). 13C-NMR (100.61 MHz, CD2Cl2, 2 diastereomers): Cation, δ = 14.20, 14.63, 14.79, 18.48, 19.15, 19.27, 20.81, 21.15, 21.36, 22.74, 24.53, 24.60, 24.74, 25.82, 25.92, 26.02, 26.14, 26.54, 26.62, 26.75, 26.86, 26.91, 27.33, 28.62 (d, J = 3.4 Hz), 30.27, 32.23 (d, J = 7.7 Hz), 32.40, 32.98 (d, J = 7.1 Hz), 34.53, 39.25 (d, J = 49.5 Hz), 39.59 (d, J = 55.6 Hz), 42.02 (d, J = 44.7 Hz), 42.57 (d, J = 34.5 Hz), 79.26 (d, J = 8.7 Hz), 81.58 (d, J = 8.5 Hz), 122.30, 127.66, 128.05, 128.18 (d, J = 8.5 Hz), 128.78, 128.92, 129.17, 129.31, 129.41, 129.50, 129.53, 130.10, 130.14 (d, J = 1.9 Hz), 132.44, 132.68, 132.75, 132.80, 134.58, 134.66, 134.73, 136.53, 136.73, 137.22, 140.65, 140.67, 141.48, 143.18, 144.06, 146.10, 148.55, 148.73, 148.78, 149.06, 153.49 (d, J = 4.0 Hz), 154.65 (d, J = 4.0 Hz), 155.66, 156.45, 200.94, 203.02; Anion, δ = 117.86 (p, J = 4.1 Hz, C-4), 125.0 (q, J = 272.5 Hz, 3-CF3 ,5-CF3), 129.3 (qq, J = 3.0, Hz, 31.3 Hz, C-3, C-5), 135.2 (br, C-2, C-6), 162.16 (q, 1J13C,11B = 49.8 Hz, C-1ipso). 11B-NMR (128.38 MHz, CD2Cl2): δ = ‒ 6.56 19F-NMR (376.46 MHz, CD2Cl2): δ = ‒ 62.85 31P{1H}-NMR (161.99 MHz, CD2Cl2, 2 diastereomers): δ = 112.08 (d, J = 20.9 Hz), 114.56 (d, J = 19.1 Hz) HRMS (ESI-TOF+) m/z calcd. for C47H58NO2PIr [M]+ 892.3834, found 892.3866 HRMS (ESI-TOF-) m/z calcd. for C32H12BF24 [M]- 863.0649, found 863.0667 Example 6: 255 mg catalyst (XI) (154 μmol) were dissolved in dry HFIP (30 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 50 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 2.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing 97% 3-benzylidenepentane-2,4-dione (160 mg, 0.825 mmol). BCS233012 FC -60- The reaction mixture was stirred at 50 dark yellow solution was allowed to get r.t. and the solvent was removed in vacuum. The residue was washed with n-pentane (2 x 10 ml), n- pentane/dichloromethane (40:1, 2 x 10 ml), n-pentane/dichloromethane (20:1, 3 x 7 ml) and n-pentane (1 x 10 ml). Drying in high vacuum gave a yellow crystalline solid (148 mg, 55% yield) consisting of a mixture of four diastereomeric iridium hydride complexes (1:0.1:0.03:0.009) of formula (XII). [Y]- wherein [Y]- is tetrakis[3,5- - 1H-NMR (400.13 MHz, CD2Cl2, 4 diastereomers): Cation, δ = -26.93 (d, J = 23.2 Hz, Ir-H), -22.08 (d, J = 22.9 Hz, Ir-H), -21.86 (d, J = 23.7 Hz, Ir-H), -21.787 (d, J = 23.8 Hz, Ir-H), 0.85 (t, J = 7.5 Hz, 3H), 0.90 (t, J = 7.5 Hz, 3H), 0.93 – 1.49 (m, 24H), 1.01 (t, J = 7.5 Hz, 3H), 1.22 (t, J = 7.5 Hz, 3H), 1.26 (t, J = 7.6 Hz, 3H), 1.50 – 1.96 (m, 12H), 1.84 (s, 3H), 1.86 (s, 3H), 1.91 (s, 3H), 1.95 – 2.06 (m, 3H), 2.08 (s, 3H), 2.15 – 2.44 (m, 5H), 2.29 (s, 3H), 2.33 (s, 3H), 2.40 (s, 3H), 2.42 (s, 3H), 2.61 (qd, J = 7.6, 1.4 Hz, 3H), 2.72 (dt, J = 16.4, 8.5 Hz, 2H), 2.79 – 2.91 (m, 2H), 2.92 – 3.06 (m, 3H), 3.63 (q, J = 18.1 Hz, 2H), 3.74 (s, 1H), 5.10 (t, J = 8.1 Hz, 1H), 5.21 (t, J = 8.1 Hz, 1H), 6.94 (s, 1H), 7.00 (s, 1H), 7.02 (s, 1H), 7.06 (s, 2H), 7.13 (s, 1H), 7.16 – 7.45 (m, 10H); Anion, δ = 7.58 (br s, 8H), 7.75 (dt, J = 5.1, 2.2 Hz, 16H). 13C-NMR (100.61 MHz, CD2Cl2, 4 diastereomers): Cation δ = 14.95, 15.66 (d, J = 4.6 Hz), 18.61, 18.77, 21.41, 21.60, 21.66, 24.69, 25.16, 25.93, 26.20, 26.43, 26.52, 26.56, 26.65, 26.69, 26.77, 26.83, 27.51, 27.62, BCS233012 FC -61- 27.74, 28.02, 28.26, 30.25, 31.49 (d, J = 8.0 Hz), 35.99, 36.03, 39.51 (d, J = 48.2 Hz), 43.55 (d, J = 45.7 Hz), 81.92 (d, J = 7.0 Hz), 83.85 (d, J = 7.6 Hz), 109.23, 110.44, 126.72, 126.80, 126.99, 127.46, 127.49, 127.67, 128.65, 128.87, 129.05, 129.09, 129.18, 130.29, 130.89, 136.97, 137.76, 140.02, 140.27, 140.34, 142.41, 144.87, 145.54, 148.32, 148.52, 155.65, 158.91, 184.39, 186.39, 187.22, 187.63; Anion, δ = 117.90 (p, J = 3.8 Hz, C-4), 125.0 (q, J = 272.7 Hz, 3-CF3 ,5-CF3), 129.3 (qq, J = 3.0, Hz, 31.5 Hz, C-3, C-5), 135.21 (br, C-2, C-6), 162.17 (q, 1J13C,11B = 49.8 Hz, C-1ipso). 11B-NMR (128.38 MHz, CD2Cl2): δ = ‒ 6.59 19F-NMR (376.46 MHz, CD2Cl2): δ = ‒ 62.84 31P{1H}-NMR (161.99 MHz, CD2Cl2, 4 diastereomers): δ = 113.22 (d, J = 21.6 Hz), 119.36 (br s), 120.92 (br s), 122.30 (d, J = 20.0 Hz) HRMS (ESI-TOF+) m/z calcd. for C44H58NO3PIr [M]+ 872.3784, found 872.3828 HRMS (ESI-TOF-) m/z calcd. for C32H12BF24 [M]- 863.0649, found 863.0662 Example 7: 188 mg catalyst (XI) (114 μmol) were dissolved in dry HFIP (23 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 50 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 2.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing 98% 2,6-dibenzylidenecyclohexanone (159.4 mg, 0.569 mmol). o The reaction mixture was stirred solution was allowed to get r.t. and the solvent was removed in vacuum. The residue was washed with n-pentane (2 x 8 ml), n- pentane/dichloromethane (40:1, 2 x 8 ml) and n-pentane (1 x 8 ml). Drying in high vacuum gave a dark red crystalline solid (174.4 mg, 84% yield) consisting of a mixture of four diastereomeric iridium hydride complexes (1:0.9:0.08:0.06) of formula (XIII). BCS233012 FC -62- + [Y]- wherein [Y]- is tetrakis - 1H-NMR (400.13 MHz, CD2Cl2, 4 diastereomers): Cation, δ = -23.11 (d, J = 26.0 Hz, Ir-H), -22.50 (d, J = 25.2 Hz, Ir-H), -21.23 (d, J = 23.4 Hz, Ir-H), -20.94 (d, J = 24.0 Hz, Ir-H), 0.35 (dq, J = 38.7, 12.8 Hz, 2H), 0.77 (t, J = 7.5 Hz, 3H), 0.81 – 1.05 (m, 8H), 1.08 (t, J = 7.5 Hz, 3H), 1.11 (t, J = 7.5 Hz, 3H), 1.14 – 1.21 (m, 3H), 1.24 (t, J = 7.6 Hz, 3H), 1.27 – 1.75 (m, 26H), 1.79 (tdd, J = 7.5, 5.6, 3.6 Hz, 4H), 2.01 – 2.20 (m, 4H), 2.24 (s, 3H), 2.30 (s, 3H), 2.35 – 2.59 (m, 6H), 2.42 (s, 3H), 2.44 (s, 3H), 2.62 – 2.89 (m, 7H), 2.94 (td, J = 6.3, 2.1 Hz, 8H), 2.97 – 3.12 (m, 4H), 5.19 (t, J = 8.3 Hz, 1H), 5.52 (t, J = 8.3 Hz, 1H), 6.92 (s, 1H), 7.01 (s, 2H), 7.02 (s, 1H), 7.05 (s, 1H), 7.07 (s, 1H), 7.13 (s, 1H), 7.18 – 7.57 (m, 17H), 7.76 (m, 4H); Anion, δ = 7.59 (br s, 8H), 7.76 (m, 16H). 13C-NMR (100.61 MHz, CD2Cl2, 4 diastereomers): Cation, δ = 15.12, 15.36, 17.58, 19.14 (d, J = 10.8 Hz), 19.99, 21.72 (d, J = 9.1 Hz), 23.37, 24.21, 24.37, 24.53, 24.57, 24.61, 24.65, 25.70, 25.84, 25.91, 26.00, 26.24, 26.37, 26.49, 26.52, 26.72, 26.86, 27.00, 27.10, 27.14, 27.21, 27.63, 28.74 (d, J = 5.8 Hz), 28.86, 29.04, 29.26, 31.15, 32.18 (d, J = 7.4 Hz), 32.75 (d, J = 7.2 Hz), 33.01, 38.38, 38.88, 39.43, 41.62 (d, J = 45.1 Hz), 42.32 (d, J = 35.8 Hz), 79.08 (d, J = 8.4 Hz), 81.33 (d, J = 8.3 Hz), 126.85, 127.22 (d, J = 4.5 Hz), 127.94, 128.05, 128.18, 128.28, 128.35, 128.41, 128.77, 128.99, 129.09, 129.13, 130.11 (d, J = 2.3 Hz), 130.18, 130.74, 131.07, 131.20, 132.36, 135.71, 135.87, 136.33, 136.38, 136.45, 136.74, 136.89, 139.82, 140.33, 141.91, 143.19, 144.26, 144.75, 144.86, 144.97, 147.07, 148.23, 148.54, 148.80, 148.94, 154.00 (d, J = 3.9 Hz), 154.98 (d, J = 3.9 Hz), 155.77, 156.68, 190.42, 200.82, 202.45; Anion, δ = 117.84 (p, J = 4.0 Hz, C-4), 124.99 (q, J = 272.4 Hz, 3-CF3 ,5-CF3), 129.27 (qq, J = 2.9, Hz, 31.4 Hz, C-3, C-5), 135.20 (br, C-2, C-6), 162.16 (q, 1J13C,11B = 49.8 Hz, C-1ipso). 11B-NMR (128.38 MHz, CD2Cl2): δ = ‒ 6.6 19F-NMR (376.46 MHz, CD2Cl2): δ = ‒ 62.56 31P{1H}-NMR (161.99 MHz, CD2Cl2, 4 diastereomers): δ 104.13 (d, J = 24.1 Hz), 113.97 (br s), 116.42 (d, J = 20.1 Hz), 114.57 (d, J = 20.9 Hz) BCS233012 FC -63- HRMS (ESI-TOF+) m/z calcd. for C52H64NO2PIr [M]+ 958.4304, found 958.4318 HRMS (ESI-TOF-) m/z calcd. for C32H12BF24 [M]- 863.0659, found 863.0662 Example 8: 255 mg catalyst (XI) (154 μmol) were dissolved in dry HFIP (30 ml) under argon by standing 30 min in ultrasound-bath. The red solution was transferred to a 50 ml Swagelok 316 stainless steel mini-reactor and hydrogenated 1 h at r.t. under 6.0 MPa H2. After completion of the hydrogenation reaction and pressure release, H2 gas was replaced by argon (addition of 2.0 MPa argon followed by pressure release to 0.1 MPa). The dark orange solution was added to a Schlenk-tube containing 98% 1,5-bis(4-methoxyphenyl)-1,4- pentadien-3-one (233 mg, 0.776 mmol). o The reaction mixture was was allowed to get r.t. and the solvent was removed in vacuum. The residue was washed with n-pentane (3 x 10 ml), n- pentane/dichloromethane (20:1, 3 x 10 ml) and n-pentane (1 x 10 ml). Drying in high vacuum gave a red crystalline solid (269 mg, 95% yield) consisting of a mixture of two diastereomeric iridium hydride complexes (1:0.9) of formula (XIV). OMe - wherein [Y]- is - BCS233012 FC -64- 1H-NMR (400.13 MHz, CD2Cl2, 2 diastereomers): Cation, δ = -22.73 (br s, Ir-H), -21.26 (br s, Ir-H), 0.41 (br s, 1H), 0.72 (t, J = 7.4 Hz, 3H), 0.76 – 0.84 (m, 5H), 0.93 – 1.38 (m, 25H), 1.27 (t, J = 7.6 Hz, 3H), 1.39 – 1.81 (m, 22H), 1.93 (s, 3H), 2.07 (s, 3H), 2.15 – 2.36 (m, 4H), 2.42 (s, 3H), 2.43 (s, 2H), 2.64 (dq, J = 14.9, 7.4 Hz, 2H), 2.70 – 2.78 (m, 1H), 2.79 – 2.90 (m, 4H), 2.91 – 3.12 (m, 4H), 3.12 – 3.25 (m, 1H), 3.84 (br s, 6H), 3.88 (s, 3H), 3.89 (s, 3H), 5.36 (br s, 1H), 6.13 (br s, 1H), 6.79 – 7.06 (m, 10H), 7.01 (s, 1H), 7.04 (s, 1H), 7.08 (s, 1H), 7.10 (s, 1H), 7.21 (s, 1H), 7.28 (s, 1H), 7.50 – 7.57 (m, 6H), 7.62 – 7.69 (m, 5H), 7.90 (d, J = 15.9 Hz, 1H); Anion, δ = 7.58 (br s, 8H), 7.76 (dt, J = 5.3, 2.3 Hz, H). 13C-NMR (100.61 MHz, CD2Cl2, 2 diastereomers): Cation, δ = 14.20, 15.06, 18.95, 19.07, 21.26 (d, J = 4.2 Hz), 22.73, 24.69, 24.93, 25.11, 26.17, 26.34, 26.39, 26.43, 26.49, 26.54, 26.57, 26.67, 26.68, 26.80, 26.89, 26.99, 27.11, 27.25, 27.96, 28.50 (d, J = 2.5 Hz), 29.70, 39.03 (d, J = 48.1 Hz), 40.59 (d, J = 50.6 Hz), 55.45, 55.78, 55.88 (d, J = 4.8 Hz), 83.01 (d, J = 7.6 Hz), 113.22, 113.88, 114.13, 114.80, 115.02 (d, J = 10.9 Hz), 122.23, 122.48, 127.61, 127.84, 129.65, 130.33, 130.56, 130.68 (br s), 130.81 (d, J = 2.9 Hz), 132.65 (br s), 134.11, 136.66, 137.77, 140.58 (br s), 141.17, 143.74, 144.37, 144.79, 145.13, 147.77, 148.06, 161.41, 161.86, 162.16, 162.92, 196.96, 201.14; Anion, δ = 117.84 (p, J = 4.0 Hz, C-4), 124.99 (q, J = 272.4 Hz, 3-CF3 ,5- CF3), 129.27 (qq, J = 2.9, Hz, 31.5 Hz, C-3, C-5), 135.20 (br, C-2, C-6), 162.15 (q, 1J13C,11B = 49.8 Hz, C- 1ipso). 11B-NMR (128.38 MHz, CD2Cl2): δ = ‒ 6.56 19F-NMR (376.46 MHz, CD2Cl2): δ = ‒ 62.83 31P{1H}-NMR (161.99 MHz, CD2Cl2, 2 diastereomers): δ = 98.31 (br s), 110.46 (br s) HRMS (ESI-TOF+) m/z calcd. for C51H64NO4PIr [M]+ 978.4203, found 978.4233 HRMS (ESI-TOF-) m/z calcd. for C32H12BF24 [M]- 863.0659, found 863.0640 Hydrogenation of a 4-substituted 1,2-dihydroquinoline: Examples 9-11: Hydrogenation reactions were performed in a H.E.L 20 ml, 316 stainless steel autoclave. Reaction mixtures were analysed without workup via HPLC (Reprosil Chiral-NR 8 μm, 150 x 4.6 mm column, 95/5 heptane/ethanol, 1 ml/min). Gas chromatography was performed on an Agilent 7890 A Series equipped with a HP5 column (30 m x 0.25 mm ID, 0.25µm film) and tetradecane was used as internal standard. Chiral iridium hydride complex (VIII-1) (catalyst loading given in Table 1) and 1.17 g 1-(2,2,4- trimethylquinolin-1(2H)-yl)ethan-1-one (5.43 mol) were dissolved in HFIP (5.0 ml). In examples 4 and 6 no additive was added. In example 5, 0.275 mmol of BF3*OEt2 were added. The reaction mixture was transferred under argon via syringe to the reactor of a H.E.L autoclave 20 ml. The autoclave was purged 5 times with 1.0 MPa H2 and then pressurized to 6.0 MPa with H2. The hydrogenation was continued at r.t. compensating the BCS233012 FC -65- gas uptake with H2. After the reaction time indicated in Table 1, pressure was released, and the autoclave was purged 5 times with 0.6 MPa argon. The reactions outcome was determined by GC analysis (diluted with EtOAc) and the enantiomeric excess by HPLC (diluted with EtOH) analysis. Results and further reaction details are given in Table 1. Table 1: Reaction Catalyst Example Catalyst time loading BF3*OEt2 Conversion Enantiomeric (min) (mol%) (mol%) GC (%a/a) excess (%ee) 9 (VIII-1) 25 1 0 100 99.3 10 (VIII-1) 25 1 10 100 99.4 11 (VIII-1) 60 0.1 0 100 98.6

Claims

BCS233012 FC -66- Claims: 1. A chiral iridium hydride complex, characterized in that the complex comprises a) a chiral chelating ligand, wherein said chiral chelating ligand comprises at least one phosphorus atom and at least one nitrogen atom that both bind to the iridium atom, and b) an enone ligand of formula (I), o wherein R1 is selected from the group consisting of hydrogen, C1-C500-alkyl, C2-C500-alkenyl, C1- C500-alkoxy, C2-C500-alkenyloxy, C1-C500-alkylamino, C2-C500-alkenylamino, di-(C1- C500-alkyl)amino, di-(C2-C500-alkenyl)amino, N-(C1-C500-alkyl)-N-(C2-C500- alkenyl)amino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8-cycloalkylamino, N-(C1- C500-alkyl)-N-(C3-C8-cycloalkyl)amino, C6-C14-aryl, wherein C1-C500-alkyl, C2-C500-alkenyl, C1-C500-alkoxy, C2-C500-alkenyloxy, C1-C500- alkylamino, C2-C500-alkenylamino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3-C8- cycloalkylamino and the C1-C500-alkyl, C2-C500-alkenyl and C3-C8-cycloalkyl residues in the di-(C1-C500-alkyl)amino, di-(C2-C500-alkenyl)amino, N-(C1-C500-alkyl)-N-(C2- C500-alkenyl)amino and N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl)amino moieties, are unsubstituted or substituted by substituent(s) independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500-haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1- C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and BCS233012 FC -67- wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1- C500-alkoxy and C1-C500-haloalkoxy, R1a is selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a C5-C7-cycloalkanone ring, wherein the C5-C7-cycloalkanone ring is unsubstituted or substituted by one to four substituents selected independently from each other from C1-C6-alkyl, and benzylidene, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, R2 is selected from the group consisting of hydrogen, C1-C500-alkyl, C1-C500-alkoxy, C1- C500-alkylamino, di-(C1-C500-alkyl)amino, C3-C8-cycloalkyl, C3-C8-cycloalkoxy, C3- C8-cycloalkylamino, N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl)amino, C6-C14-aryl, wherein C1-C500-alkyl, C1-C500-alkoxy, C1-C500-alkylamino, C3-C8-cycloalkyl, C3-C8- cycloalkoxy, C3-C8-cycloalkylamino and the C1-C500-alkyl and C3-C8-cycloalkyl residues in the di-(C1-C500-alkyl)amino and N-(C1-C500-alkyl)-N-(C3-C8- cycloalkyl)amino moieties, are unsubstituted or substituted by substituent(s) independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500-haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1- C500-alkoxy and C1-C500-haloalkoxy, and the arrow indicates a bond to the iridium atom. 2. The chiral iridium hydride complex according to claim 1, wherein R1a is selected from the group consisting of hydrogen and acetyl, or BCS233012 FC -68- R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, wherein the benzylidene is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C6-alkyl, and C1-C6-alkoxy. 3. The chiral iridium hydride complex according to claim 1, wherein R1a is hydrogen. 4. The chiral iridium hydride complex according to claim 1, wherein R1 is selected from the group consisting of C1-C500-alkyl, C2-C500-alkenyl, C6-C14-aryl, wherein C1-C500-alkyl and C2-C500-alkenyl are unsubstituted or substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500- haloalkyl, and C1-C500-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl. 5. The chiral iridium hydride complex according to claim 1, wherein R1 is selected from the group consisting of C1-C3-alkyl and vinyl, wherein the vinyl is substituted by phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, or R1 is phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl. 6. The chiral iridium hydride complex according to any one of claims 1 to 5, wherein R2 is selected from the group consisting of C1-C500-alkyl, C6-C14-aryl, BCS233012 FC -69- wherein C1-C500-alkyl is unsubstituted or substituted by substituent(s) independently selected from the group consisting of halogen, hydroxy, C1-C500-alkoxy, C1-C500- haloalkyl, C1-C500-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C500-alkyl, C1-C500-alkoxy, C1-C500-haloalkyl, and C1-C500-haloalkoxy, and wherein the C6-C14-aryl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C500-alkyl, C1-C500-haloalkyl, C1- C500-alkoxy and C1-C500-haloalkoxy. 7. The chiral iridium hydride complex according to any one of claims 1 to 5, wherein R2 is phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C100-alkyl, C1-C100-haloalkyl, C1- C100-alkoxy and C1-C100-haloalkoxy. 8. The chiral iridium hydride complex according to claim 1, wherein R1 is methyl, phenyl, styryl or para-methoxystyryl, R1a is hydrogen or acetyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, and R2 is phenyl or para-methoxyphenyl. 9. The chiral iridium hydride complex according to any one of claims 1 to 8, wherein the chiral chelating ligand is a ligand of formula (IIa), (IIb), (IIIa), (IIIb), (IVa) or (IVb), m BCS233012 FC -70- (IIa) (IIb) (IVa) (IVb) wherein R3, R4 and R5 are independently from one another selected from the group consisting of hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6- alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C6-C14-aryl and C6-C14-aryl-C1-C4- alkyl, wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C7-cycloalkyl and the C3-C7- cycloalkyl in the C3-C7-cycloalkyl-C1-C4-alkyl moiety are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl and C1-C4-haloalkoxy, and wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1-C6-alkyl substituents, R6 and R7 are independently from one another selected from the group consisting of C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C4-alkyl, C6-C14-aryl, C6-C14-aryloxy, C6-C14-aryl-C1-C4-alkyl, piperidinyl and pyridyl, BCS233012 FC -71- wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and di(C1-C6- alkyl)amino, are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl, C6-C14-aryloxy and C3-C12-cycloalkyl, in each case as such or as part of a composite substituent, are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4- haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five C1- C6-alkyl substituents, or R6 and R7 together with the phosphorus atom which they are bound to, form a phospholane ring, which is unsubstituted or substituted with one or two C1-C6-alkyl groups, or R6 and R7 together form in which are atom, p and q are independently from one another selected from 0, 1 and 2, R11 and R12 are independently selected from C1-C6-alkyl and phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1- C4-alkyl, C1-C4-alkoxy and phenyl, which is unsubstituted or substituted by one or two C1- C4-alkyl substituents, m is 1 or 2, R8 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C4- alkyl, C1-C4-alkyl-C3-C7-cycloalkyl, C6-C14-aryl or C6-C14-aryl-C1-C4-alkyl, BCS233012 FC -72- wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R9 and R10 are independently from one another selected from the group consisting of C1-C6- alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, di(C1-C6-alkyl)amino, C3-C12-cycloalkyl, C3-C12-cycloalkyl-C1-C4-alkyl, C6-C14-aryl, C6-C14-aryloxy and C6-C14-aryl-C1-C4-alkyl, wherein the C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy and di(C1-C6- alkyl)amino, are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4-haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, phenyl, C1-C4-alkoxy, C1-C4- haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl, the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl, the C6-C14-aryloxy and C3-C12-cycloalkyl, in each case as such or as part of a composite substituent, are unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, phenyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R9 and R10 together with the phosphorus atom which they are bound to, form a phospholane ring, which is unsubstituted or substituted with one or two C1-C6-alkyl groups, or R9 and R10 together form in which are atom, p and q are independently from one another selected from 0, 1 and 2, and R11 and R12 are independently selected from C1-C6-alkyl and phenyl, which is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1- BCS233012 FC -73- C4-alkyl, C1-C4-alkoxy and phenyl, which is unsubstituted or substituted by one or two C1- C4-alkyl substituents, A is # , atom and in which the bond identified by "#" is bound directly to the oxazoline moiety, 13 R1 R and 4 are from one another selected from the group consisting of hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C12-cycloalkyl, C3-C7-cycloalkyl-C1-C4-alkyl, C1-C4-alkyl-C3-C7-cycloalkyl, C6-C14-aryl and C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, or R13 and R14 together with the carbon which they are bound to, form a C5-C6-cycloalkyl ring, R15 is selected from phenyl, benzyl, t-butyl, isopropyl, cyclohexyl, R16 is selected from hydrogen, methyl, ethyl, isopropyl, each R17 is independently selected from hydrogen, benzyl, methyl, ethyl, and each R18 is independently selected from cyclohexyl, phenyl, 2-methylphenyl, 4-methylphenyl, 2,6- dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl. 10. The chiral iridium hydride complex according to claim 9, wherein the chiral chelating ligand is a ligand of formula (IIa) or (IIb), wherein R3 is a group of formula BCS233012 FC -74- , wherein ** denotes the bond to the 6,7-dihydro-5H-cyclopenta[b]pyridine moiety, R19 is hydrogen, methyl or ethyl, and R20 is C1-C6-alkyl, R4 is hydrogen, R5 is C1-C4 alkyl or phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4- alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, R6 and R7 are independently from one another selected from the group consisting of C1-C6- alkyl, C3-C8-cycloalkyl, piperidinyl and pyridyl, and m is 1. 11. The chiral iridium hydride complex according to claim 9, wherein the chiral chelating ligand is a ligand of formula (IIa) or (IIb), wherein R3 is 2,6-diethyl-4-methylphenyl, R4 is hydrogen, R5 is methyl, and R6 and R7 are each cyclohexyl, and m is 1. BCS233012 FC -75- 12. The chiral iridium hydride complex according to any one of claims 1 to 11, wherein the chiral iridium hydride complex is a complex of formula (V) [IrH(L*)(L(I))]Y, (V) wherein L* is the chiral chelating ligand of formula (IIa), (IIb), (IIIa), (IIIb), (IVa) or (IVb), L(I) is the enone ligand of formula (I), and Y is a non-coordinating anion selected from the group consisting of [B(R21)4]-, PF6-, SbF6-, CF3SO3-, [Al{OC(CF3)3}4]− (VI) and ^-TRISPHAT (VII) I (VI) (VII) wherein R21 is selected from fluorine and phenyl, which is unsubstituted or substituted with one to five substituents selected from C1-C4-alkyl, C1-C4-haloalkyl and halogen. 13. The chiral iridium hydride complex according to claim 12, wherein L* is the chiral chelating ligand of formula (IIa) or (IIb), wherein R3 is 2,6-diethyl-4-methylphenyl, R4 is hydrogen, R5 is methyl, and BCS233012 FC -76- R6 and R7 are each cyclohexyl, and m is 1, L(I) is the enone ligand of formula (I), wherein R1 is methyl, phenyl, styryl or para-methoxystyryl, R1a is hydrogen or acetyl, or R1a and R1 form together with the carbon atom to which R1a is attached and the carbonyl group to which R1 is attached a cyclohexanone ring, wherein the cyclohexanone ring is substituted by one benzylidene group in ortho position to the carbonyl group, and R2 is phenyl or para-methoxyphenyl, and Y is a non-coordinating anion selected from the group consisting of [B(R21)4]- and [Al{OC(CF3)3}4]− of formula (VI), wherein R21 is 3,5-bis(trifluoromethyl)phenyl or 2,3,4,5,6-pentafluorophenyl. 14. A process for preparing a compound of formula (IXa) or (IXb), 25 25 (R26)n O R O R (R26)n wherein R22 is selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy- C1-C6-alkyl, C3-C6-cycloalkyl, C6-C14-aryl, or C6-C14-aryl-C1-C4-alkyl, BCS233012 FC -77- wherein the C1-C6-alkyl, C3-C6-cycloalkyl and the C1-C6-alkoxy in the C1-C6-alkoxy- C1-C6-alkyl moiety, are unsubstituted or substituted by 1 to 3 substituents independently selected from the group consisting of halogen, C1-C4-alkoxy, C1-C4- haloalkyl, C1-C4-haloalkoxy and phenyl, wherein the phenyl is unsubstituted or substituted by one to five substituents selected independently from each other from halogen, C1-C4-alkyl, C1-C4-alkoxy, C1-C4-haloalkyl, and C1-C4-haloalkoxy, and wherein the C6-C14-aryl and the C6-C14-aryl in the C6-C14-aryl-C1-C4-alkyl moiety in each case is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4- haloalkoxy, R23 and R24 are the same and are selected from the group consisting of hydrogen, C1-C6-alkyl, C1- C6-haloalkyl and C1-C6-alkoxy-C1-C6-alkyl, or R23 and R24 together with the carbon which they are bound to, form a C3-C6-cycloalkyl ring, R25 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6- alkylamino, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C4- alkyl, C2-C6-alkenyloxy, 9-flurorenylmethyleneoxy, C6-C14-aryl, C6-C14-aryloxy, C6- C14-aryl-C1-C4-alkyloxy or C6-C14-aryl-C1-C4-alkyl, wherein the C6-C14-aryl as such or as part of a composite substituent is unsubstituted or substituted by one to five substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy, n is 0, 1, 2, 3 or 4, and each substituent R26, if present, is independently selected from the group consisting of halogen, C1- C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, hydroxyl, amino and –C(=O)-C1-C6-alkyl, comprising enantioselective hydrogenation of a compound of formula (X) BCS233012 FC -78- (R26)n wherein the substituents integer n are each as defined for the compound of the formula (IXa) or (IXb), characterized in that the process is conducted in presence of a chiral iridium hydride complex as defined in any of claims 1 to 13. 15. The process according to claim 14, wherein R22 is C1-C4-alkyl, R23 and R24 are methyl, R25 is C1-C4-alkyl, n is 0 or 1, and R26 if present, is fluorine.
EP24732726.5A 2023-06-23 2024-06-19 Chiral iridium hydride catalysts for enantioselective hydrogenation of 4-substituted 1,2- dihydroquinolines Pending EP4731635A1 (en)

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