JP4063875B2 - ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用 - Google Patents

ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用 Download PDF

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Publication number
JP4063875B2
JP4063875B2 JP51955697A JP51955697A JP4063875B2 JP 4063875 B2 JP4063875 B2 JP 4063875B2 JP 51955697 A JP51955697 A JP 51955697A JP 51955697 A JP51955697 A JP 51955697A JP 4063875 B2 JP4063875 B2 JP 4063875B2
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catalyst
ligand
acetate
substrate
hydrogenation
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JP51955697A
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Japanese (ja)
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JPH10513402A (ja
JPH10513402A5 (enExample
Inventor
ラオテンシュトラウホ ヴァレンティン
ピー エム ヴァンヘッシェ コンラート
ジュネ ジャン−ピエール
ルノワル ジャン−イヴ
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Firmenich SA
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Firmenich SA
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    • 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
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/1875—Phosphinites (R2P(OR), their isomeric phosphine oxides (R3P=O) and RO-substitution derivatives thereof)
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
    • 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
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2428—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom
    • B01J31/2433—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member with more than one complexing phosphine-P atom comprising aliphatic or saturated rings
    • 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
    • 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
    • B01J31/2457—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 comprising aliphatic or saturated rings, e.g. Xantphos
    • 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
    • C07C67/303—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by hydrogenation of unsaturated carbon-to-carbon 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
    • 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
    • B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
    • B01J2531/0202—Polynuclearity
    • B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
    • 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
    • B01J2531/84—Metals of the iron group
    • B01J2531/842—Iron
    • 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
    • B01J31/22—Organic complexes
    • B01J31/2282—Unsaturated compounds used as ligands
    • B01J31/2291—Olefins

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP51955697A 1995-11-22 1996-11-20 ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用 Expired - Lifetime JP4063875B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH3300/95 1995-11-22
CH330095 1995-11-22
CH162196 1996-06-28
CH1621/96 1996-06-28
PCT/IB1996/001263 WO1997018894A1 (fr) 1995-11-22 1996-11-20 Catalyseurs de ruthenium et leur utilisation dans l'hydrogenation asymetrique de cyclopentenones

Publications (3)

Publication Number Publication Date
JPH10513402A JPH10513402A (ja) 1998-12-22
JPH10513402A5 JPH10513402A5 (enExample) 2004-10-21
JP4063875B2 true JP4063875B2 (ja) 2008-03-19

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Application Number Title Priority Date Filing Date
JP51955697A Expired - Lifetime JP4063875B2 (ja) 1995-11-22 1996-11-20 ルテニウム触媒及びシクロペンテノン類の不斉水素化に於けるその使用

Country Status (6)

Country Link
US (1) US5874600A (enExample)
EP (1) EP0810903B1 (enExample)
JP (1) JP4063875B2 (enExample)
DE (1) DE69602586T2 (enExample)
ES (1) ES2136437T3 (enExample)
WO (1) WO1997018894A1 (enExample)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2750423B1 (fr) * 1996-06-28 1998-08-14 Rhone Poulenc Chimie Procede d'hydrogenation asymetrique d'un compose cetonique
WO1998052687A1 (en) * 1997-05-20 1998-11-26 Firmenich S.A. Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates
US6214763B1 (en) 1997-05-20 2001-04-10 Firmenich Sa Ruthenium catalysts and their use in the asymmetric hydrogenation of weakly coordinating substrates
NL1007776C2 (nl) * 1997-12-12 1999-06-15 Dsm Nv Katalysator voor de bereiding van chirale producten in optisch actieve vorm.
GB9807888D0 (en) 1998-04-09 1998-06-10 Chirotech Technology Ltd Asymmetric hydrogenation
WO1999031041A1 (en) * 1997-12-17 1999-06-24 Chirotech Technology Limited Asymmetric hydrogenation
WO1999052852A1 (en) * 1998-04-09 1999-10-21 Chirotech Technology Limited Asymmetric hydrogenation
US6280519B1 (en) * 1998-05-05 2001-08-28 Exxon Chemical Patents Inc. Environmentally preferred fluids and fluid blends
US6586620B1 (en) 1999-11-05 2003-07-01 Firmenich Sa Process for the preparation of alkyl 3-oxo-2-pentyl-1-cyclopenteneacetates
US7494927B2 (en) 2000-05-15 2009-02-24 Asm International N.V. Method of growing electrical conductors
WO2002057227A2 (en) * 2001-01-19 2002-07-25 Rhodia/Chirex, Inc. Process of enantiomerically enriched flavor and fragrance components
JP4005800B2 (ja) * 2001-12-10 2007-11-14 高砂香料工業株式会社 新規不斉ホスフィン配位子
US7250538B2 (en) * 2002-09-26 2007-07-31 Shell Oil Company Process for the hydroformylation of an ethylenically unsaturated compound
ATE461913T1 (de) * 2003-05-09 2010-04-15 Solvias Ag Phospholansalze und deren verwendung in der enantioselektive hydrierung
JP4667027B2 (ja) * 2004-12-09 2011-04-06 旭化成イーマテリアルズ株式会社 シス−２、３−ジ置換シクロペンタノンの製造方法
US8025922B2 (en) 2005-03-15 2011-09-27 Asm International N.V. Enhanced deposition of noble metals
US7666773B2 (en) 2005-03-15 2010-02-23 Asm International N.V. Selective deposition of noble metal thin films
EP1900720B1 (en) * 2005-06-30 2012-06-13 Asahi Kasei Chemicals Corporation Process for production of substituted cyclopentanone
US20070014919A1 (en) * 2005-07-15 2007-01-18 Jani Hamalainen Atomic layer deposition of noble metal oxides
US7435484B2 (en) * 2006-09-01 2008-10-14 Asm Japan K.K. Ruthenium thin film-formed structure
US20090087339A1 (en) * 2007-09-28 2009-04-02 Asm Japan K.K. METHOD FOR FORMING RUTHENIUM COMPLEX FILM USING Beta-DIKETONE-COORDINATED RUTHENIUM PRECURSOR
AR070841A1 (es) * 2008-03-13 2010-05-05 Bial Portela & Ca Sa Proceso de hidrogenacion catalitica asimetrica
US8084104B2 (en) 2008-08-29 2011-12-27 Asm Japan K.K. Atomic composition controlled ruthenium alloy film formed by plasma-enhanced atomic layer deposition
US9379011B2 (en) 2008-12-19 2016-06-28 Asm International N.V. Methods for depositing nickel films and for making nickel silicide and nickel germanide
US20110020546A1 (en) * 2009-05-15 2011-01-27 Asm International N.V. Low Temperature ALD of Noble Metals
US8871617B2 (en) 2011-04-22 2014-10-28 Asm Ip Holding B.V. Deposition and reduction of mixed metal oxide thin films
US9607842B1 (en) 2015-10-02 2017-03-28 Asm Ip Holding B.V. Methods of forming metal silicides
CN110475763B (zh) 2017-03-31 2023-01-20 国际香料和香精公司 制备脱氢希蒂莺的化学方法
TW202200828A (zh) 2020-06-24 2022-01-01 荷蘭商Ａｓｍ Ｉｐ私人控股有限公司 含鉬薄膜的氣相沉積

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NL6918228A (en) * 1969-12-04 1971-06-08 Aliphatic keto-esters used in perfumes
FR2651152B1 (fr) * 1989-08-23 1991-11-29 Elf Aquitaine Perfectionnement a la preparation de catalyseurs chiraux a base de complexes du ruthenium et du phosphore.
JP2775335B2 (ja) * 1990-08-01 1998-07-16 高砂香料工業株式会社 ルテニウム―ホスフィン錯体及びその製造中間体
US5304524A (en) * 1991-06-17 1994-04-19 Ethyl Corporation Asymmetric hydrogenation of aromatic-substituted olefins using organoruthenium catalyst
FR2693190B1 (fr) * 1992-07-02 1994-09-23 Elf Aquitaine Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO.
US5728866A (en) * 1994-06-23 1998-03-17 Firmenich Sa Process for the preparation of (+)-(1R) -cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid

Also Published As

Publication number Publication date
US5874600A (en) 1999-02-23
EP0810903A1 (fr) 1997-12-10
EP0810903B1 (fr) 1999-05-26
ES2136437T3 (es) 1999-11-16
DE69602586D1 (de) 1999-07-01
JPH10513402A (ja) 1998-12-22
DE69602586T2 (de) 2000-03-02
WO1997018894A1 (fr) 1997-05-29

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