DE69307706D1 - Verfahren zur enantioselektiven hydrierung der carbonylgruppe unter verwendung von ruthenium komplexen mit biphosphineliganden - Google Patents

Verfahren zur enantioselektiven hydrierung der carbonylgruppe unter verwendung von ruthenium komplexen mit biphosphineliganden

Info

Publication number
DE69307706D1
DE69307706D1 DE69307706T DE69307706T DE69307706D1 DE 69307706 D1 DE69307706 D1 DE 69307706D1 DE 69307706 T DE69307706 T DE 69307706T DE 69307706 T DE69307706 T DE 69307706T DE 69307706 D1 DE69307706 D1 DE 69307706D1
Authority
DE
Germany
Prior art keywords
pct
enantioselectively
hydrating
carbonyl group
sec
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.)
Expired - Fee Related
Application number
DE69307706T
Other languages
English (en)
Other versions
DE69307706T2 (de
Inventor
Jean-Pierre Genet
Sylvain Juge
Jean-Alex Laffitte
Catherine Pinel
Serge Mallart
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.)
Societe National Elf Aquitaine
Original Assignee
Societe National Elf Aquitaine
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 Societe National Elf Aquitaine filed Critical Societe National Elf Aquitaine
Publication of DE69307706D1 publication Critical patent/DE69307706D1/de
Application granted granted Critical
Publication of DE69307706T2 publication Critical patent/DE69307706T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

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
    • B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
    • B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
    • B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
    • 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
    • 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
    • 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
    • B01J31/2414—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 comprising aliphatic or saturated rings
    • 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
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • B01J2231/643—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of R2C=O or R2C=NR (R= C, H)
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0261—Complexes comprising ligands with non-tetrahedral chirality
    • B01J2531/0266—Axially chiral or atropisomeric ligands, e.g. bulky biaryls such as donor-substituted binaphthalenes, e.g. "BINAP" or "BINOL"
    • 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
DE69307706T 1992-07-02 1993-06-30 Verfahren zur enantioselektiven hydrierung der carbonylgruppe unter verwendung von ruthenium komplexen mit biphosphineliganden Expired - Fee Related DE69307706T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9208160A FR2693190B1 (fr) 1992-07-02 1992-07-02 Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO.
PCT/FR1993/000663 WO1994001390A1 (fr) 1992-07-02 1993-06-30 Procede d'hydrogenation enantioselectif du groupe carbonyl, utilisant des complexes de ruthenium avec biphosphine ligands

Publications (2)

Publication Number Publication Date
DE69307706D1 true DE69307706D1 (de) 1997-03-06
DE69307706T2 DE69307706T2 (de) 1997-07-24

Family

ID=9431455

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69307706T Expired - Fee Related DE69307706T2 (de) 1992-07-02 1993-06-30 Verfahren zur enantioselektiven hydrierung der carbonylgruppe unter verwendung von ruthenium komplexen mit biphosphineliganden

Country Status (8)

Country Link
US (1) US5614641A (de)
EP (1) EP0648201B1 (de)
AT (1) ATE148091T1 (de)
CA (1) CA2139361A1 (de)
DE (1) DE69307706T2 (de)
ES (1) ES2099453T3 (de)
FR (1) FR2693190B1 (de)
WO (1) WO1994001390A1 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69602586T2 (de) * 1995-11-22 2000-03-02 Firmenich & Cie Rutheniumkatalysatoren und deren verwendung zur asymmetrischen cyclopentenonhydrierung
DE19548399A1 (de) * 1995-12-22 1997-06-26 Basf Ag Rutheniumkomplexe mit einem chiralen, zweizähnigen Phosphinoxazolin-Liganden zur enantioselektiven Transferhydrierung von prochiralen Ketonen
WO1997037765A1 (en) * 1996-04-04 1997-10-16 Bp Chemicals Limited Novel catalyst composition
FR2750423B1 (fr) * 1996-06-28 1998-08-14 Rhone Poulenc Chimie Procede d'hydrogenation asymetrique d'un compose cetonique
ES2212287T3 (es) * 1997-05-20 2004-07-16 Firmenich Sa Catalizadores de rutenio y su uso en la hidrogenacion asimetrica de sustratos debilmente coordinantes.
US6214763B1 (en) 1997-05-20 2001-04-10 Firmenich Sa Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates
IT1303757B1 (it) * 1998-11-16 2001-02-23 Sigma Tau Ind Farmaceuti Processo industriale per la produzione di l-carnitina.
FR2788269B1 (fr) * 1999-01-08 2001-02-09 Rhodia Chimie Sa Procede de preparation d'un ether de type benzylique
EP1366004B1 (de) * 2000-09-13 2008-05-14 Firmenich S.A. Katalytisches hydrierungsverfahren
US6462206B1 (en) 2001-06-20 2002-10-08 E. I. Du Pont De Nemours And Company Catalytic reduction of ketones and aldehydes using organometallic ruthenium complexes
WO2003040082A1 (fr) * 2001-10-24 2003-05-15 Kaneka Corporation Procede de production d'un derive d'acide 3,5-dihydroxycarboxylique optiquement actif
JP3566955B2 (ja) 2001-12-28 2004-09-15 関東化学株式会社 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法
CN100384791C (zh) * 2002-12-02 2008-04-30 索尔维亚斯股份公司 碳-杂原子双键的催化氢化
BRPI0618114A2 (pt) * 2005-11-02 2011-08-16 Hoffmann La Roche ligantes de fosfina quiral c, p bidentados complexos de metal e de metal de transição, uso dos referidos complexos e processo para hidrogenação assimétrica de um composto olefìnico ou cetÈnico pró-quiral e para a fabricação dos referidos ligantes
CN113399000B (zh) * 2021-06-01 2022-07-12 万华化学集团股份有限公司 一种催化剂及其制备方法、催化剂组合物，及环氧化合物制备直链醇的方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343741A (en) * 1981-04-22 1982-08-10 Hoffmann-La Roche Inc. Chiral phosphines
EP0158875B1 (de) * 1984-04-19 1989-12-13 F. Hoffmann-La Roche Ag Chirale Rhodium-diphosphinkomplexe für asymmetrische Hydrierungen
JPH0699367B2 (ja) * 1987-06-11 1994-12-07 高砂香料工業株式会社 光学活性アルコ−ルの製法
JPH064544B2 (ja) * 1987-06-19 1994-01-19 高砂香料工業株式会社 光学活性アルコ−ルの製造方法
JPH0678277B2 (ja) * 1988-02-19 1994-10-05 高砂香料工業株式会社 光学活性アルコールおよびその誘導体の製造方法
JP2739254B2 (ja) * 1990-10-01 1998-04-15 高砂香料工業株式会社 イリジウム―光学活性ホスフィン錯体及びこれを用いた光学活性アルコールの製造方法
EP0484271B1 (de) * 1990-11-02 1994-10-19 Ciba-Geigy Ag Verfahren zur Herstellung von optisch aktiven aliphatischen Hydroxycarbonsäureestern
FR2671079B1 (fr) * 1990-12-28 1994-06-03 Elf Aquitaine Procede d'hydrogenation de composes organiques et catalyseurs au ruthenium pour sa realisation.
JP2850068B2 (ja) * 1991-10-22 1999-01-27 高砂香料工業株式会社 ルテニウム−ホスフィン錯体及びこれを触媒とする光学活性１−置換−１，３−プロパンジオールの製造方法
JP2736947B2 (ja) * 1991-11-21 1998-04-08 高砂香料工業株式会社 水溶性なスルホン酸アルカリ金属塩置換ビナフチルホスフイン遷移金属錯体及びこれを用いた不斉水素化法
JP3369558B2 (ja) * 1992-01-31 2003-01-20 エフ・ホフマン−ラ ロシユ アーゲー 燐化合物
JP3310056B2 (ja) * 1992-07-16 2002-07-29 高砂香料工業株式会社 光学活性４−メチル−２−オキセタノンの製造方法
US5481008A (en) * 1993-09-13 1996-01-02 Hoffmann-La Roche Inc. Process for the preparation of optically active compounds

Also Published As

Publication number Publication date
US5614641A (en) 1997-03-25
WO1994001390A1 (fr) 1994-01-20
ES2099453T3 (es) 1997-05-16
CA2139361A1 (en) 1994-01-20
EP0648201B1 (de) 1997-01-22
ATE148091T1 (de) 1997-02-15
EP0648201A1 (de) 1995-04-19
FR2693190B1 (fr) 1994-09-23
DE69307706T2 (de) 1997-07-24
FR2693190A1 (fr) 1994-01-07

Similar Documents

Publication Publication Date Title
DE69307706T2 (de) Verfahren zur enantioselektiven hydrierung der carbonylgruppe unter verwendung von ruthenium komplexen mit biphosphineliganden
DK0582692T3 (da) Diphosphinligander
CA2116420A1 (en) Ferrocene diphosphines as ligands for homogeneous catalysts
ATE232854T1 (de) Verfahren zur herstellung von 9-desoxotaxanen
DE69511740D1 (de) Wasserlösliche Phosphin-Derivate
ATE135008T1 (de) Chirale phosphine
ATE147398T1 (de) 3,4-dimethyl-2,5-6-tris(p-sulfonatophenyl)-1- phosphanorbornadien, verfahren zu seiner herstellung und verfahren zur hydroformylierung von olefinisch ungesättigten verbindungen
DE69104999T2 (de) Verfahren zur hydrierung von olefinischen ungesättigten verbindungen ud ruthenium-katalysatoren zu ihrer durchführung.
ATE337327T1 (de) Substituierte ferrocenyldiphosphinligande für homogene hydrogenieringskatalysatoren
ATE146465T1 (de) Verfahren zur enantioselektiven hydrierung von 2h-pyran-2-on-derivaten
ATE496880T1 (de) Prozess zur hydrierung von nicht-aktivierten iminen unter verwendung von ruthenium-komplexen als katalysatoren
DE69617496T2 (de) Optisch-aktive tertiäre Phosphinverbindungen, sie enthaltende Übergangsmetallkomplexe als Liganden und Verfahren zur Herstellung optisch-aktiver Siliciumverbindungen mittels solcher Übergangsmetallkomplexe
ATE216690T1 (de) Verfahren zur asymmetrischen hydrierung von ketonverbindungen und ihren derivaten
ATE206704T1 (de) Verfahren zur herstellung von optisch aktivem 1- (p-methoxybenzyl)-1,2,3,4,5,6,7,8- octahydroisochinolin
ES2125072T3 (es) Procedimiento para la eliminacion de recubrimientos contaminantes en las superficies metalicas.
DE69429616T2 (de) Desallyherungsreagenz und verfahren zur desallyherung unter verwendung dieses reagenzes
DE69620437D1 (de) Verfahren zur herstellung von optisch aktivem 2-substituiertem tetrahydropyran-4-on
ATE192437T1 (de) Verfahren zur herstellung von 3-amino-2-chlor-4- alkyl- bzw. 4-cycloalkyl-pyridine
ATE210627T1 (de) Verfahren zur herstellung von optisch aktiven alpha-substituierten benzylalkoholen
ATE225769T1 (de) Verfahren zur herstellung von arylmercaptanen durch hydrierung von diaryldisulfiden
ATE154024T1 (de) Neue bis(aminomethyl)phosphinsäure-derivate und verfahren zur herstellung von bis(aminomethyl)phosphinsäure-derivaten
ATE187958T1 (de) Verfahren zur herstellung von levobupivacain und analogue aus l-lysin
ATE101339T1 (de) Verfahren zur herstellung eines riechstoffes.

Legal Events

Date Code Title Description
8364 No opposition during term of opposition
8339 Ceased/non-payment of the annual fee