CN1208295C - 在锌催化剂存在下通过硅烷还原羰基化合物 - Google Patents

在锌催化剂存在下通过硅烷还原羰基化合物 Download PDF

Info

Publication number
CN1208295C
CN1208295C CNB998004243A CN99800424A CN1208295C CN 1208295 C CN1208295 C CN 1208295C CN B998004243 A CNB998004243 A CN B998004243A CN 99800424 A CN99800424 A CN 99800424A CN 1208295 C CN1208295 C CN 1208295C
Authority
CN
China
Prior art keywords
zinc
ligand
oil
compound
reduction
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 - Lifetime
Application number
CNB998004243A
Other languages
English (en)
Chinese (zh)
Other versions
CN1262667A (zh
Inventor
于贝尔·米蒙
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.)
Firmenich SA
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Publication of CN1262667A publication Critical patent/CN1262667A/zh
Application granted granted Critical
Publication of CN1208295C publication Critical patent/CN1208295C/zh
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • 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
    • B01J31/1805—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 nitrogen
    • 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
    • B01J31/1805—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 nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • 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
    • B01J31/1805—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 nitrogen
    • B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
    • B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2239—Bridging ligands, e.g. OAc in Cr2(OAc)4, Pt4(OAc)8 or dicarboxylate 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
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/2243—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/02—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains containing only carbon and hydrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • 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
    • 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
    • B01J2531/0213—Complexes without C-metal linkages
    • B01J2531/0216—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
    • B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
    • B01J2531/26—Zinc
    • 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
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
    • C07C2602/28—Hydrogenated naphthalenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyridine Compounds (AREA)
CNB998004243A 1998-04-01 1999-02-25 在锌催化剂存在下通过硅烷还原羰基化合物 Expired - Lifetime CN1208295C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH778/1998 1998-04-01
CH77898 1998-04-01

Publications (2)

Publication Number Publication Date
CN1262667A CN1262667A (zh) 2000-08-09
CN1208295C true CN1208295C (zh) 2005-06-29

Family

ID=4194974

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB998004243A Expired - Lifetime CN1208295C (zh) 1998-04-01 1999-02-25 在锌催化剂存在下通过硅烷还原羰基化合物

Country Status (10)

Country Link
US (3) US6245952B1 (enExample)
EP (1) EP0986527B1 (enExample)
JP (1) JP4169801B2 (enExample)
CN (1) CN1208295C (enExample)
AT (1) ATE239685T1 (enExample)
CA (1) CA2291486A1 (enExample)
DE (1) DE69907589T2 (enExample)
ES (1) ES2198886T3 (enExample)
IL (1) IL133270A (enExample)
WO (1) WO1999050211A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1012131B1 (fr) * 1997-09-09 2003-03-19 Firmenich Sa Reduction enantioselective de cetones avec un systeme agent silanique/compose metallique/ligand chiral
CA2291486A1 (en) * 1998-04-01 1999-10-07 Firmenich S.A. Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst
JP2002516828A (ja) * 1998-06-01 2002-06-11 アンソニー・ジェイ・バービスカー 局所経皮治療
US7955611B2 (en) 2000-01-03 2011-06-07 International Flora Technologies Ltd. Binding and rinse-off of quaternary ammonium compounds for cosmetic and personal care applications
DE10238114A1 (de) * 2002-08-21 2004-03-04 Bayer Ag Optisch aktive Diamine und deren Anwendung in katalytischen Prozessen
JP4962924B2 (ja) * 2005-03-04 2012-06-27 学校法人東京理科大学 光学活性アルコールの製造方法
JP5179430B2 (ja) * 2009-02-27 2013-04-10 国立大学法人名古屋大学 光学活性アルコールの製造方法
CN101844957B (zh) * 2010-03-30 2012-10-24 杭州师范大学 一种α, β-不饱和酮羰基还原成亚甲基的方法
WO2014096566A1 (fr) * 2012-12-20 2014-06-26 Bluestar Silicones France Sas Composition organopolysiloxanique vulcanisable a temperature ambiante en elastomere et nouveaux catalyseurs de polycondensation d'organopolysiloxanes
FR2999980A1 (fr) * 2012-12-20 2014-06-27 Bluestar Silicones France Article presentant des proprietes antisalissures et destine a etre utilise dans des applications aquatiques en particulier marines
CN104981523B (zh) * 2012-12-20 2018-10-09 埃肯有机硅法国简易股份公司 在环境温度下可硫化成弹性体的有机聚硅氧烷组合物以及有机聚硅氧烷缩聚催化剂
EP2935492B1 (fr) * 2012-12-20 2016-10-26 Bluestar Silicones France SAS Article présentant des propriétés antisalissures et destiné à être utilisé dans des applications aquatiques en particulier marines
CN106062011B (zh) * 2014-05-21 2018-03-16 道康宁公司 含锌催化剂、制备含锌催化剂的方法以及包含含锌催化剂的组合物
JP6514568B2 (ja) * 2015-05-19 2019-05-15 東ソー・ファインケム株式会社 ジアルキル亜鉛部分加水分解物含有溶液及びこの溶液を用いる酸化亜鉛薄膜の製造方法
EP4234522A3 (en) 2015-11-18 2023-10-25 Provivi, Inc. Production of fatty olefin derivatives via olefin metathesis
WO2018150379A2 (en) 2017-02-17 2018-08-23 Provivi, Inc. Synthesis of pheromones and related materials via olefin metathesis
EP3438158B1 (de) 2017-08-01 2020-11-25 Evonik Operations GmbH Herstellung von sioc-verknüpften polyethersiloxanen
WO2021247583A1 (en) 2020-06-01 2021-12-09 Provivi, Inc. Synthesis of pheromone derivatives via z-selective olefin metathesis
MX2023005170A (es) * 2020-11-27 2023-05-30 Firmenich & Cie Reduccion mediante un silano en presencia de catalizador de zinc.
CN116874350A (zh) * 2023-07-10 2023-10-13 福建桦智工程技术有限公司 一种使用不饱和酯连续还原制备叶醇的工艺

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3061424A (en) 1957-02-06 1962-10-30 Wacker Chemie Gmbh Method of reducing organometallic compounds
GB8902228D0 (en) * 1989-02-01 1989-03-22 Ici Plc Carbodiimide-isocyanurate rigid foams
US5220020A (en) 1990-11-21 1993-06-15 Massachusetts Institute Of Technology Catalytic reduction of organic carbonyls using metal catalysts
US5227538A (en) * 1990-11-21 1993-07-13 Massachusetts Institute Of Technology Catalytic asymmetric reduction of ketones using metal catalysts
US5449736A (en) * 1993-07-16 1995-09-12 Research Foundation Of The State Of New York Water soluble phosphorylated polysiloxanes
ES2137542T3 (es) * 1994-10-19 1999-12-16 Firmenich & Cie Procedimiento para la preparacion de alcoholes.
EP1012131B1 (fr) * 1997-09-09 2003-03-19 Firmenich Sa Reduction enantioselective de cetones avec un systeme agent silanique/compose metallique/ligand chiral
CA2291486A1 (en) * 1998-04-01 1999-10-07 Firmenich S.A. Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst

Also Published As

Publication number Publication date
DE69907589T2 (de) 2004-03-25
JP2002503259A (ja) 2002-01-29
US6245952B1 (en) 2001-06-12
EP0986527B1 (en) 2003-05-07
WO1999050211A1 (en) 1999-10-07
JP4169801B2 (ja) 2008-10-22
EP0986527A1 (en) 2000-03-22
CN1262667A (zh) 2000-08-09
CA2291486A1 (en) 1999-10-07
ES2198886T3 (es) 2004-02-01
US6533960B2 (en) 2003-03-18
US20010034464A1 (en) 2001-10-25
IL133270A (en) 2006-06-11
US20030171210A1 (en) 2003-09-11
DE69907589D1 (de) 2003-06-12
US6770588B2 (en) 2004-08-03
IL133270A0 (en) 2001-04-30
ATE239685T1 (de) 2003-05-15

Similar Documents

Publication Publication Date Title
CN1208295C (zh) 在锌催化剂存在下通过硅烷还原羰基化合物
CN1091087C (zh) 制备醇的方法
CN1202052C (zh) 用硅烷剂/金属化合物/手性配位体实施酮的对映体选择性还原反应
CN1151745A (zh) 双配位膦配体
CN1059906C (zh) 水溶性膦衍生物
Mukaiyama et al. Chiral pyrrolidine diamines as efficient ligands in asymmetric synthesis
CN101039894A (zh) 生产光学活性的羰基化合物的方法
CN1056865A (zh) 用于生产1，3-二醇和/或3-羟基醛的催化剂和制备方法及其应用
CN1247193A (zh) 戊醛及其制备方法
CN1204271A (zh) 钌/锡双金属催化剂的制备方法
CN1138744C (zh) 旋光菊酸的制备方法
CN1174545A (zh) 醛的制备方法
JP5564506B2 (ja) アルミニウム錯体と分子内閉環反応における触媒としてのその使用
JP4635343B2 (ja) 光学活性な銅錯体ならびに光学活性なサリチリデンアミノアルコール化合物およびそれを用いる光学活性なシクロプロパンカルボン酸誘導体の製造方法
US7009079B2 (en) Chiral copper complex and production processes thereof and using the same
JP4860481B2 (ja) 大環状ケトン類の製造方法およびその中間体
CN1572782A (zh) 制备氟苯基亚烷基酸衍生物的方法
MXPA99011062A (en) Reduction of carbonyl compounds by a silane in the presence of a zinc catalyst
CN1464875A (zh) 有机金属配合物和使用有机金属配合物的催化剂、以及羧酸酯的制备方法
JP2001278851A (ja) 不斉銅錯体の製造法およびそれを用いる光学活性シクロプロパン化合物の製造法
JP2023550901A (ja) 亜鉛触媒存在下におけるシランによる還元
CN1724525A (zh) γ－丁内酯衍生物及其制备方法
JPH10195084A (ja) 重合性トリオルガノシリル不飽和カルボキシレートの製造法
CN101052610A (zh) 环戊烯酮的合成
FR2474491A1 (fr) Procede de fabrication d'imines d'aminoacides allyl-substituees convertibles notamment en a-aminoacides

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
CX01 Expiry of patent term

Granted publication date: 20050629

CX01 Expiry of patent term