EP1628985A2 - Ligands chiraux et leurs complexes de metaux de transition - Google Patents

Ligands chiraux et leurs complexes de metaux de transition

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Publication number
EP1628985A2
EP1628985A2 EP04733263A EP04733263A EP1628985A2 EP 1628985 A2 EP1628985 A2 EP 1628985A2 EP 04733263 A EP04733263 A EP 04733263A EP 04733263 A EP04733263 A EP 04733263A EP 1628985 A2 EP1628985 A2 EP 1628985A2
Authority
EP
European Patent Office
Prior art keywords
hept
trimethylbicyclo
pyridine
compounds
transition metal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04733263A
Other languages
German (de)
English (en)
Inventor
Ulrich Scholz
Björn SCHLUMMER
Paul Knochel
Tanasri Bunlaksananusorn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Saltigo GmbH
Original Assignee
Lanxess Deutschland GmbH
Saltigo GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Lanxess Deutschland GmbH, Saltigo GmbH filed Critical Lanxess Deutschland GmbH
Publication of EP1628985A2 publication Critical patent/EP1628985A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • 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
    • 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
    • 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
    • C07F15/004—Iridium compounds without a metal-carbon linkage
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems

Definitions

  • the present invention relates to chiral nitrogen-phosphorus compounds and their transition metal complexes and the use of these transition metal complexes, in particular in asymmetric syntheses.
  • Enantiomerically enriched chiral compounds are valuable starting substances for the production of agrochemicals and pharmaceuticals.
  • Asymmetric catalysis has been used for the synthesis of such enantiomerically enriched chirals
  • R 1 and R 2 each independently represent an optionally substituted hydrocarbon radical with a total of 1 to 18 carbon atoms
  • a * stands for a carbodivalent, cyclic and optionally substituted radical with a total of 5 to 18 carbon atoms, which as such
  • Symmetry element has no mirror plane.
  • Alkyl or alkylene or alkoxy each independently means a straight-chain, cyclic, branched or unbranched alkyl- or alkylene or alkoxy radical. The same applies to the non-aromatic part of an arylalkyl radical.
  • C 1 -C 4 -alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl, C 1 -C 8 -alkyl furthermore, for example, n-pentyl,
  • -C-C 8 alkoxy is, for example, methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy and tert-butoxy, n-pentoxy, neo-pentoxy, cyclo-hexoxy, cyclo-pentoxy , n-hexoxy and n-octoxy, CrC 12 alkoxy furthermore for example for adamantoxy, the isomeric menthoxy radicals, n-decoxy and n-dodecoxy.
  • C 2 -C 20 alkenyl is, for example, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 1-hexenyl, 1-heptenyl, 1-octenyl or 2-octenyl.
  • Fluoroalkyl each independently means a straight-chain, cyclic, branched or unbranched alkyl radical which is substituted once, several times or completely by fluorine atoms.
  • C 1 -C 2 o-fluoroalkyl represents trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, nonafluorobutyl, perfluorooctyl, perfluorododecyl and perfluorohexadecyl.
  • Aryl stands for a heteroaromatic radical with 5 to 18 carbon atoms in which none, one, two or three carbon atoms per cycle, in total
  • Molecule at least one carbon atom can be substituted by heteroatoms selected from the group nitrogen, sulfur or oxygen, however, preferably for a carbocyclic aromatic radical having 6 to 18 skeletal carbon atoms.
  • carbocyclic aromatic radicals with 6 to 18 carbon atoms are, for example, phenyl, naphthyl, phenanthrenyl, anthracenyl or fluorenyl, heteroaromatic radicals with 5 to 18 carbon atoms in which none, one, two or three carbon atoms per cycle, but at least one carbon atom in the entire molecule , Heteroatoms, selected from the group nitrogen, sulfur or oxygen, may be substituted, for example pyridinyl, oxazolyl, benzofuranyl, dibenzoftrranyl or quinolinyl.
  • COO (CC 8 alkyl), CON (-C 8 alkyl) 2 , COO -Cs arylalkyl), COO (C 4 -C 14 aryl), CO CrCs alkyl), C 5 -C 5 arylalkyl or Tri CrCe-alkyrjsiloxyl.
  • Azoaryl represents a heteroaromatic radical with 5 to 18 carbon atoms in which none, one, two or three carbon atoms per cycle, but at least one carbon atom in the entire molecule, but at least one carbon atom, can be substituted by heteroatoms, at least one nitrogen atom and optionally further heteroatoms are selected from the group nitrogen,
  • Arylalkyl each independently means a straight-chain, cyclic, branched or unbranched alkyl radical which can be replaced simply, repeatedly or completely by aryl
  • C 5 -C 1 arylalkyl is, for example, benzyl, 1-phenylethyl, 1-phenylpropyl, 2-phenylpropyl and 1-naphthylmethyl, and optionally the isomeric or stereoisomeric forms.
  • Arylalkenyl each independently means a straight-chain, cyclic, branched or unbranched alkenyl radical which can be substituted once, several times or completely by aryl radicals as defined above.
  • C 6 -C 1 arylalkenyl represents, for example, 1-phenylvinyl or 2-phenylvinyl.
  • a * is a carbodivalent and cyclic radical
  • the conformative mobility of the ethylene bridge carrying the Het and PR R 2 radicals is usually severely restricted.
  • the residues Het and PR R are preferably arranged transposed to one another.
  • Stereomerically enriched compounds of the formula (I) are preferred. Enriched with stereomers in the sense of the invention means that one stereomer is present in a larger relative proportion than the respective other stereomers.
  • the other stereoisomers can be both enantiomers and diastereomers.
  • the relative amount of substance of only one stereoisomer, based on the sum of all stereoisomers, is preferably at least 90%, particularly preferably at least 95% and very particularly preferably at least 98.5%.
  • R and R are preferably each independently of the other: C 1 -C 2 -alkyl,
  • R 1 and R 2 ' are particularly preferably each identical: C 3 -C 12 -alkyl, C -C 14 -
  • R and R> 2 very particularly preferably each represent: iso-propyl, tert-butyl, cyclohexyl, phenyl, 2- (C 1 -C 8 ) alkylphenyl such as o-tolyl, 3- (C 1 -C 8 ) -alkylphenyl such as m-tolyl, 4- (C 1 -C 8 ) -alkylphenyl such as p-tolyl, 2,6-di- (C 1 -C 8 ) -alkylphenyl such as 2,6-
  • C 8 ) -alkoxyphenyl such as 2,6-dimethoxyphenyl, 3,5-di- (-C-C 8 ) alkoxyphenyl such as 3,5-di ethoxyphenyl, 3,4,5-tri- (C -C 8 ) alkoxyphenyl such as 3,4,5-trimethoxyphenyl, 3,5-dialkyl-4- (C 1 -C 8 ) alkoxyphenyl such as 3,5-dimethyl-4-anisyl, 3,5- (C 1 -C 8 ) dialkyl -4- di- (CrC 8 ) -alkylaminophenyl, 3,5-dimethyl-4-dimethylamino-phenyl, 4-di- (Ci-C 8 ) -alkylaminophenyl such as 4-diethylaminophenyl and 4-dimethylaminophenyl, 3,5-bis -
  • [(C 1 -C 4 ) -fluoroalkyl] phenyl such as 3,5-bis-trifluoromethyl-phenyl, 2,4-bis - [(-C-C 4 ) -fluoro-alkyl] phenyl such as 2,4-bis-trifluoromethyl-phenyl, 4 - [(C 1 -C 4 ) -fluoroalkyl] phenyl such as 4-trifluoromethylphenyl and phenyl substituted by one, two, three, four or five times by fluorine and / or chlorine, fluorenyl or naphthyl such as 4-fluorophenyl and 4-chlorine - phenyl and furanyl.
  • Azoaryl is preferably 2-pyridyl or 2-quinolyl, it being possible for the radicals mentioned to be further substituted by one, two or three radicals which are each independently selected from the group chlorine, bromine, fluorine, C 1 -C 12 -alkyl, C 4 -C ⁇ o-AryL C 5 -C n arylalkyl and CC 12 alkoxy.
  • Azoaryl very particularly preferably represents 2-pyridyl, 6-bromo-2-pyridyl, 6-phenyl-2-pyridyl and 2-quinolyl.
  • Particularly preferred compounds of the formula (I) are those of the formulas (Ia) and (1b)
  • R, R and Het have the meanings and preferred ranges given above.
  • the compounds of the formula (I) or (la) and (Ib) can be prepared, for example, starting from compounds of the formula (II) according to the scheme below.
  • X 1 and X 2 each independently represent chlorine, bromine, iodine or a sulfonate, preferably bromine, iodine or a C 1 -C -perfluoroalkyl sulfonate.
  • the metalation can be carried out, for example, in such a way that the compounds of the formula (DI) are converted in a manner known per se into an analogous organozinc or organomagnesium compound and this is then reacted with compounds of the formula (H) in the presence of a catalyst to give compounds of the formula ( IN) are implemented.
  • Palladium or nickel complexes for example, can be used as the catalyst in step a).
  • Preferred compounds of the formula (IN) are those of the formulas (INa) and (INb):
  • Step b) can be carried out in such a way that Neritatien of formula (N) in the presence of a base, which can at least partially deprotonate the Neritatien of formula (N) in the presence of a solvent to compounds of formula (I).
  • Preferred bases are alcoholates, preferred solvents sulfoxides such as dimethyl sulfoxide, sulfones such as tetramethylene sulfone or secondary carboxamides such as dimethylformamide or ⁇ -methylpyrrolidone.
  • step b) the compounds of the formula (IN) can be reacted according to the following scheme in a step c) by reaction with Neritatien of the formula (NT) to Neritatien of the formula (NU) and in a step d) the Neritatien of the formula ( VIT) to reduce compounds of formula (I).
  • Step c) can be carried out completely analogously to step b), step d) in a manner known per se, for example by reduction with silanes such as in particular trichlorosilane in the presence of a base such as in particular triethylamine.
  • the method comprising steps c) and d) can be of advantage in particular when using electron-rich phosphines of the formula (IJT).
  • Preferred compounds of the formula (VIT) are those of the formulas (VIIa) and
  • the invention furthermore comprises transition metal complexes which contain the compound of the formula (I) according to the invention. Transition metal complexes which contain stereoisomerically enriched Neritatien of formula (I) are preferred.
  • Transition metal complexes are preferably complexes of ruthenium, osmium,
  • Cobalt rhodium, iridium, nickel, palladium, platinum and copper, particularly preferably complexes of ruthenium, rhodium, iridium, nickel and palladium and particularly preferably complexes of palladium and iridium.
  • transition metal complexes according to the invention are particularly suitable as
  • the invention therefore also includes catalysts which contain the transition metal complexes according to the invention.
  • Isolated transition metal complexes which contain the Neritatien of formula (I) are preferably those in which the ratio of transition metal to compound of formula (I) is 1: 1.
  • L 1 in each case represents a C 2 -C 12 alkene such as, for example, ethylene or cyclooctene or a nitrile such as, for example, acetonitrile, benzonitrile or benzyl nitrile, or
  • L ] 2 together represents a (C 4 -C 2 ) -diene such as, for example, bicyclo [2.1.1] hepta-2,5-diene ( ⁇ orbornadiene) or 1,5-cyclooctadiene and
  • a non or weakly coordinating anion such as methanesulfonate, trifluoromethanesulfonate, tetrafluoroborate, hexafluorophosphate,
  • transition metal complexes are those which can be obtained by reacting transition metal compounds and compounds of the formula (I).
  • Suitable transition metal compounds are, for example, those of the formula
  • q stands for rhodium, iridium and ruthenium for 3, for nickel, palladium and platinum for 2 and for copper for 1,
  • L 1 each represents a C 2 -C 12 alkene such as, for example, ethylene or cyclooctene or a nitrile such as, for example, acetonitrile, benzonitrile or benzyl nitrile, or
  • L 2 together represents a (C 4 -C 12 ) diene such as, for example, bicyclo [2.1.1] hepta-2,5-diene (norbornadiene) or 1,5-cyclooctadiene
  • L 2 represents aryl radicals such as, for example, cymol, mesityl, phenyl or cyclooctadiene, norbornadiene or methylallyl
  • L 3 stands for (C 4 -C 12 ) diene such as, for example, bicyclo [2.1.1] hepta-2,5-diene (norbornadiene) or 1,5-cyclooctadiene and
  • An 4 for a non or weakly coordinating anion such as methanesulfonate, trifluoromethanesulfonate, tetrafluoroborate, hexafluorophosphate, Perchlorate, hexafluoroantimonate, tetra (bis-3,5-trifluromethylphenyl) borate or tetraphenyl borate.
  • transition metal compounds are, for example, Ni (1,5-cyclo-octadiene) 2 , Pd 2 (dibenzylidene acetone) 3 , Pd [PPh 3 ], cyclopentadienyl 2 Ru,
  • Metal content for example 25 to 200 mol% based on the one used
  • Compound of the formula (I) are preferably 50 to 150 mol%, very particularly preferably 75 to 125 mol% and even more preferably 100 to 115 mol%.
  • the catalysts which contain the transition metal complexes according to the invention are particularly suitable for 1,4-additions, allylic substitutions, hydroboration, hydroformylation, hydrocyanation, Heck reactions and hydrogenation.
  • the catalysts contain transition metal complexes which contain stereoisomerically enriched compounds of the formula (I), the catalysts are particularly suitable for carrying out the above-mentioned reactions asymmetrically.
  • bonds such as prochiral imines.
  • the invention therefore also encompasses a process for the preparation of stereoisomerically enriched, preferably enantiomerically enriched compounds, which is characterized in that the compounds which are stereoisomerically enriched, preferably enantiomerically enriched, either by catalytic hydrogenation of olefms, enamines, enamides, imines or ketones or by
  • Hydroboration of alkenes and, if appropriate, subsequent oxidation or are obtained by allylic substitution and the catalysts used are those which contain transition metal complexes of stereoisomerically enriched compounds of the formula (I) with the meaning given there.
  • the transition metal complex can be, for example, 0.001 to 5 mol%, based on the metal content, based on the substrate used, preferably 0.001 to 0.5 mol%, very particularly preferably 0.001 to 0.1 mol%.
  • asymmetric hydrogenation, asymmetric hydroboration can be carried out, for example, in such a way that the catalyst is optionally produced from a transition metal compound and a stereoisomerically enriched compound of the formula (I) in a suitable solvent, the substrate is added and the reaction mixture is placed under hydrogen pressure at the reaction temperature become or a suitable one
  • asymmetric allylic substitutions can be carried out, for example, in such a way that the catalyst consists of a transition metal compound and a stereoisomerically enriched compound of
  • Formula (I) is optionally generated in a suitable solvent and the substrate and the nucleophile are added.
  • catalysts are preferably used which contain iridium compounds of the formula (I) and for allylic ones
  • Substitutions are preferably used catalysts which contain palladium complexes of compounds of formula (I).
  • the catalysts of the invention are particularly suitable in a process for the preparation of stereoisomerically enriched, preferably enantiomerically enriched, active ingredients of medicaments and agricultural chemicals, or intermediates of these two classes.
  • the advantage of the present invention is that the ligands can be produced in an efficient manner and their electronic and steric properties are variable over a wide range starting from readily available starting materials.
  • 'Furthermore, according to the invention show ligands and their transition metal complexes, especially in asymmetric hydrogenations, allylic substitutions hydroboration and good enantioselectivity and conversion rates.
  • Example 3 Analogously to Example 3, the product mentioned above was started from 2,6-disbromopyridine in a yield of 70% of theory. Th. Received.
  • Example 3 Analogously to Example 3, the product mentioned above was started from 2-bromopyridine and the vinyl triflate from Example 2 in a yield of 85% of theory. Th. Received.
  • Example 10 Analogously to Example 10, the product mentioned above was started with the compound from Example 6 with diphenylphosphine oxide in a yield of 86% of theory. Th. Received.
  • Example 10 Analogously to Example 10, the product mentioned above was started with the compound from Example 9 with diphenylphosphine oxide in a yield of 78% of theory. Th. Received.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Quinoline Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

La présente invention concerne des composés de phosphore chiraux et leurs complexes de métaux de transition, ainsi que l'utilisation desdits complexes de métaux de transition, en particulier dans des synthèses asymétriques.
EP04733263A 2003-05-22 2004-05-15 Ligands chiraux et leurs complexes de metaux de transition Withdrawn EP1628985A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10323692A DE10323692A1 (de) 2003-05-22 2003-05-22 Chirale Liganden und deren Übergangsmetallkomplexe
PCT/EP2004/005251 WO2004104014A2 (fr) 2003-05-22 2004-05-15 Ligands chiraux et leurs complexes de metaux de transition

Publications (1)

Publication Number Publication Date
EP1628985A2 true EP1628985A2 (fr) 2006-03-01

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EP04733263A Withdrawn EP1628985A2 (fr) 2003-05-22 2004-05-15 Ligands chiraux et leurs complexes de metaux de transition

Country Status (6)

Country Link
US (1) US20070066825A1 (fr)
EP (1) EP1628985A2 (fr)
JP (1) JP2006526001A (fr)
CN (1) CN1791607A (fr)
DE (1) DE10323692A1 (fr)
WO (1) WO2004104014A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009046469A (ja) * 2007-07-26 2009-03-05 Chiba Univ 光学活性アリル化合物類の製造方法
US8076480B2 (en) * 2007-07-26 2011-12-13 National University Corporation Chiba University Process of preparing optically active allyl compound
CN105665025B (zh) * 2014-01-07 2018-02-02 中国科学院上海有机化学研究所 一种pnn配体‑钴络合物催化剂及其制备方法和应用
CN112175006A (zh) * 2020-11-10 2021-01-05 河南省科学院化学研究所有限公司 一种吡啶二苯基膦衍生物的制备方法

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Title
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WO2004104014A2 (fr) 2004-12-02
CN1791607A (zh) 2006-06-21
WO2004104014A3 (fr) 2005-03-17
US20070066825A1 (en) 2007-03-22
JP2006526001A (ja) 2006-11-16
DE10323692A1 (de) 2004-12-09

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