WO2008117054A3 - Chiral diphosphines, methods for their preparation, transition metal complexes comprising them and use in chiral synthesis - Google Patents

Chiral diphosphines, methods for their preparation, transition metal complexes comprising them and use in chiral synthesis Download PDF

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Publication number
WO2008117054A3
WO2008117054A3 PCT/GB2008/001053 GB2008001053W WO2008117054A3 WO 2008117054 A3 WO2008117054 A3 WO 2008117054A3 GB 2008001053 W GB2008001053 W GB 2008001053W WO 2008117054 A3 WO2008117054 A3 WO 2008117054A3
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WO
WIPO (PCT)
Prior art keywords
chiral
preparation
methods
transition metal
metal complexes
Prior art date
Application number
PCT/GB2008/001053
Other languages
French (fr)
Other versions
WO2008117054A2 (en
Inventor
Declan Gilheany
Graham R Cumming
Gary King
Matthias Voegler
Vladimir Larichev
Original Assignee
Celtic Catalysts Ltd
Declan Gilheany
Graham R Cumming
Gary King
Matthias Voegler
Vladimir Larichev
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 Celtic Catalysts Ltd, Declan Gilheany, Graham R Cumming, Gary King, Matthias Voegler, Vladimir Larichev filed Critical Celtic Catalysts Ltd
Priority to EP08718887A priority Critical patent/EP2139905A2/en
Priority to US12/593,292 priority patent/US8067642B2/en
Priority to CA002682335A priority patent/CA2682335A1/en
Priority to JP2010500354A priority patent/JP2010522733A/en
Publication of WO2008117054A2 publication Critical patent/WO2008117054A2/en
Publication of WO2008117054A3 publication Critical patent/WO2008117054A3/en

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2409—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring with more than one complexing phosphine-P atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/283—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon bonds
    • 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
    • C07F15/006—Palladium compounds
    • C07F15/0066—Palladium 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5027—Polyphosphines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/821—Ruthenium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The present invention provides P-chiral compounds of general formulae (II) and (III): in formula (II) at least one of R21, R25, R26 and R30 is independently selected from CM alkyl, CF3, C1 -4 alkoxy, phenyl and benzyloxy and the remaining substituents selected from R21, R25. R26 and R30 are hydrogen; at least one of R22, R24, R27 and R29 are independently selected from C1-14 alkyl, CF3, C1-14 alkoxy, phenyl and benzyloxy and the remaining substituents selected, from R22, R24, R27 and R29 are hydrogen; and R23 and R28 are independently selected from hydrogen, CM alkyl, CF3, , C1-14 alkoxy, phenyl and benzyloxy;. in formula (III) at least one of R21, R25, R26 and R30 is independently selected from phenyl and benzyloxy and the remaining substituents selected from R21, R25, R-26 and R30 are hydrogen; and R22, R-23 R24, R27, R28 and R29 are independently selected from hydrogen, C1-14 alkyl, CF3, C1-14 alkoxy, phenyl and benzyloxy.
PCT/GB2008/001053 2007-03-28 2008-03-28 Chiral diphosphines, methods for their preparation, transition metal complexes comprising them and use in chiral synthesis WO2008117054A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP08718887A EP2139905A2 (en) 2007-03-28 2008-03-28 Chiral diphospines, methods for their preparation, transition metal complexes comprising them and use in chiral synthesis
US12/593,292 US8067642B2 (en) 2007-03-28 2008-03-28 Chiral phosphorous compounds
CA002682335A CA2682335A1 (en) 2007-03-28 2008-03-28 Chiral phosphorus compounds
JP2010500354A JP2010522733A (en) 2007-03-28 2008-03-28 Chiral phosphorus compounds

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0707379.4A GB0707379D0 (en) 2007-03-28 2007-03-28 Chiral phosphorus compounds
GB0707379.4 2007-03-28

Publications (2)

Publication Number Publication Date
WO2008117054A2 WO2008117054A2 (en) 2008-10-02
WO2008117054A3 true WO2008117054A3 (en) 2008-11-13

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2008/001053 WO2008117054A2 (en) 2007-03-28 2008-03-28 Chiral diphosphines, methods for their preparation, transition metal complexes comprising them and use in chiral synthesis

Country Status (6)

Country Link
US (1) US8067642B2 (en)
EP (1) EP2139905A2 (en)
JP (1) JP2010522733A (en)
CA (1) CA2682335A1 (en)
GB (1) GB0707379D0 (en)
WO (1) WO2008117054A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8803099B2 (en) * 2012-06-06 2014-08-12 Canon Kabushiki Kaisha Compound, scintillator, and radiation detector
CN114133412B (en) * 2021-11-30 2023-11-07 河南工程学院 Preparation method of chiral 1, 2-bis [ (2-methoxyphenyl) phenylphosphinyl ] ethane

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1466803A (en) * 1973-12-03 1977-03-09 Monsanto Co Optically active bissphosphines and metal complex catalysts containing them
US4230641A (en) * 1977-11-21 1980-10-28 Air Products And Chemicals, Inc. Hydroformylation of olefins

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4434293A1 (en) * 1994-09-19 1996-03-21 Christian Dr Doebler Prepn. of 3- and 4-pyridyl alanine and its derivs.
FR2887253A1 (en) * 2005-06-20 2006-12-22 Phosphoenix Sarl New optically active organo phosphorus compound useful to prepare phosphine-metal catalysts useful to carry out asymmetrical syntheses in organic chemistry

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1466803A (en) * 1973-12-03 1977-03-09 Monsanto Co Optically active bissphosphines and metal complex catalysts containing them
US4230641A (en) * 1977-11-21 1980-10-28 Air Products And Chemicals, Inc. Hydroformylation of olefins

Non-Patent Citations (7)

* Cited by examiner, † Cited by third party
Title
BRUNNER H ET AL: "Asymmetrische Katalysen, 88. Kinetik der Rh-katalysierten Hydrierung von (Z)-(alpha)-N-Acetylaminozimtsäure mit optisch aktiven Schalenphosphinen als Liganden", ZEITSCHRIFT FUR NATURFORSCHUNG, TEIL B:ANORGANISCHE CHEMIE, ORGANISCHE CHEMIE, vol. 49, no. 9, 1 September 1994 (1994-09-01), pages 1305 - 1307, XP000466909, ISSN: 0932-0776 *
BRUNNER H ET AL: "Enantioselektive Katalyse. LXXXI. Optisch aktive Zweischalenphosphine", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 454, no. 1/02, 27 July 1993 (1993-07-27), pages 87 - 94, XP000576108, ISSN: 0022-328X *
CASEY C P ET AL: "Electronically dissymmetric DIPHOS derivatives give higher n:i regioselecttivity in rhodium-catalyzed hydroformylation than either of their symmetric counterparts", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 121, no. 1, 13 January 1999 (1999-01-13), pages 63 - 70, XP000789493, ISSN: 0002-7863 *
CREPY K V L ET AL: "Recent developments in catalytic asymmetric hydrogenation employing P-chirogenic diphosphine ligands", ADVANCED SYNTHESIS & CATALYSIS, vol. 345, no. 1,2, 2003, pages 79 - 101, XP009060886, ISSN: 1615-4150 *
KAGAN H B: "ASymmetric catalysis in organic synthesis with industrial perspectives", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, no. 5, 1988, pages 846 - 853, XP009103754 *
KNOWLES W S: "Application of organometallic catalysts to the commercial production of L-DOPA", JOURNAL OF CHEMICAL EDUCATION, vol. 63, March 1986 (1986-03-01), pages 222 - 225, XP009103627 *
WADA Y ET AL: "Optically pure 1,2-bis[(o-alkylphenyl)phenylphosphino]ethanes and their use in rhodium-catalysed asymmetric hydrogenations of alpha-(acylamino)acrylic derivatives", ADVANCED SYNTHESIS & CATALYSIS, vol. 346, no. 7, June 2004 (2004-06-01), pages 777 - 788, XP007905279, ISSN: 1615-4150 *

Also Published As

Publication number Publication date
EP2139905A2 (en) 2010-01-06
US20100168456A1 (en) 2010-07-01
CA2682335A1 (en) 2008-10-02
US8067642B2 (en) 2011-11-29
JP2010522733A (en) 2010-07-08
WO2008117054A2 (en) 2008-10-02
GB0707379D0 (en) 2007-05-23

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