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WO1991016322A3 - Ligands chiraux heterocycliques et procede de dihydroxylation asymetrique catalytique d'olefines - Google Patents

Ligands chiraux heterocycliques et procede de dihydroxylation asymetrique catalytique d'olefines Download PDF

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Publication number
WO1991016322A3
WO1991016322A3 PCT/US1991/002778 US9102778W WO9116322A3 WO 1991016322 A3 WO1991016322 A3 WO 1991016322A3 US 9102778 W US9102778 W US 9102778W WO 9116322 A3 WO9116322 A3 WO 9116322A3
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WO
WIPO (PCT)
Prior art keywords
olefin
osmium
combined
derivative
chiral ligand
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.)
Ceased
Application number
PCT/US1991/002778
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English (en)
Other versions
WO1991016322A2 (fr
Inventor
Declan Gilheany
Byeong Moon Kim
Hoi-Lun Kwong
K Barry Sharpless
Tomoyuki Shibata
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Massachusetts Institute of Technology
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Massachusetts Institute of Technology
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Publication date
Application filed by Massachusetts Institute of Technology filed Critical Massachusetts Institute of Technology
Priority to CA002081315A priority Critical patent/CA2081315C/fr
Priority to US07/775,683 priority patent/US5260461A/en
Publication of WO1991016322A2 publication Critical patent/WO1991016322A2/fr
Publication of WO1991016322A3 publication Critical patent/WO1991016322A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne des procédés d'adjonction à une oléfine sous catalyse par osmium. Selon le procédé de dihydroxylation asymétrique présenté, une oléfine, un ligand chiral, un solvant organique, de l'eau, un oxydant et un composé contenant de l'osmium sont combinés. Selon le procédé de l'oxyamination asymétrique, une oléfine, un ligand chiral, un solvant organique, de l'eau, un dérivé de métallochloramine, un composé contenant de l'osmium et, éventuellement, un composé d'ammonium de tétraalkyle sont combinés. Selon le procédé de la diamination asymétrique, une oléfine, un ligand chiral, un solvant organique, un dérivé de métallochloramine, une amine et un composé contenant de l'osmium sont combinés. Selon une variante, une oléfine, un ligand chiral qui est un dérivé de dihydroquinidine polymère ou un dérivé de dihydroquinine, de l'acétone, de l'eau, une base, un oxydant et du tétroxyde d'osmium sont combinés pour provoquer une dihydroxylation asymétrique de l'oléfine.
PCT/US1991/002778 1988-01-11 1991-04-23 Ligands chiraux heterocycliques et procede de dihydroxylation asymetrique catalytique d'olefines Ceased WO1991016322A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CA002081315A CA2081315C (fr) 1990-04-23 1991-04-23 Ligands chiraux heterocycliques et methode de dihydroxylation catalytique asymetrique d'olefines
US07/775,683 US5260461A (en) 1988-01-11 1991-10-10 Ligands for ADH: cinchona alkaloids and moderately sized organic substituents linked through a planar aromatic spacer group

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/512,934 US5126494A (en) 1988-01-11 1990-04-23 Methods for catalytic asymmetric dihydroxylation of olefins
US512,934 1990-04-23

Publications (2)

Publication Number Publication Date
WO1991016322A2 WO1991016322A2 (fr) 1991-10-31
WO1991016322A3 true WO1991016322A3 (fr) 1992-03-05

Family

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Family Applications (1)

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PCT/US1991/002778 Ceased WO1991016322A2 (fr) 1988-01-11 1991-04-23 Ligands chiraux heterocycliques et procede de dihydroxylation asymetrique catalytique d'olefines

Country Status (5)

Country Link
US (1) US5126494A (fr)
EP (1) EP0526582A1 (fr)
JP (2) JP3177244B2 (fr)
CA (1) CA2081315C (fr)
WO (1) WO1991016322A2 (fr)

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US5260461A (en) * 1988-01-11 1993-11-09 Massachusetts Institute Of Technology Ligands for ADH: cinchona alkaloids and moderately sized organic substituents linked through a planar aromatic spacer group
US5516929A (en) * 1988-01-11 1996-05-14 Massachusetts Institute Of Technology Method for catalytic asymmetric dihydroxylation of olefins using heterocyclic chiral ligands
EP0543969A1 (fr) * 1991-05-13 1993-06-02 Massachusetts Institute Of Technology Ligands chiraux heterocycliques et procede de dihydroxylation asymetrique et catalytique d'olefines
US5302257A (en) * 1992-02-21 1994-04-12 Sepracor, Inc. Electrocatalytic asymmetric dihydroxylation of olefinic compounds
US5491237A (en) 1994-05-03 1996-02-13 Glaxo Wellcome Inc. Intermediates in pharmaceutical camptothecin preparation
US5420366A (en) * 1994-05-11 1995-05-30 Hoechst Celanese Corporation Process for the preparation of optically active 2-arylcyclohexanols
US6262278B1 (en) 1995-03-14 2001-07-17 President And Fellows Of Harvard College Stereoselective ring opening reactions
US5665890A (en) * 1995-03-14 1997-09-09 President And Fellows Of Harvard College Stereoselective ring opening reactions
ATE207919T1 (de) * 1995-08-03 2001-11-15 Dade Behring Inc Chinidin-konjugate und ihre anwendung in immunoassays
US5850086A (en) * 1996-06-21 1998-12-15 Regents Of The University Of Minnesota Iron complexes for bleach activation and stereospecific oxidation
US6559309B2 (en) 1996-11-01 2003-05-06 Osi Pharmaceuticals, Inc. Preparation of a camptothecin derivative by intramolecular cyclisation
US6133485A (en) * 1998-04-15 2000-10-17 Synphar Laboratories, Inc. Asymmetric synthesis of 2-(2,4-difluorophenyl)-1-heterocycl-1-yl butan-2,3-diols
US20020058774A1 (en) 2000-09-06 2002-05-16 Kurth Thomas M. Transesterified polyol having selectable and increased functionality and urethane material products formed using the polyol
US6180686B1 (en) * 1998-09-17 2001-01-30 Thomas M. Kurth Cellular plastic material
US7063877B2 (en) 1998-09-17 2006-06-20 Urethane Soy Systems Company, Inc. Bio-based carpet material
US20030191274A1 (en) * 2001-10-10 2003-10-09 Kurth Thomas M. Oxylated vegetable-based polyol having increased functionality and urethane material formed using the polyol
US6979477B2 (en) 2000-09-06 2005-12-27 Urethane Soy Systems Company Vegetable oil-based coating and method for application
US6962636B2 (en) * 1998-09-17 2005-11-08 Urethane Soy Systems Company, Inc. Method of producing a bio-based carpet material
US8575226B2 (en) * 1998-09-17 2013-11-05 Rhino Linings Corporation Vegetable oil-based coating and method for application
US6596870B2 (en) 2000-07-13 2003-07-22 Brandeis University Asymmetric synthetic methods based on phase transfer catalysis
US6646102B2 (en) 2001-07-05 2003-11-11 Dow Global Technologies Inc. Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom
US6700001B2 (en) 2001-10-05 2004-03-02 Wyeth Process for stereoselective synthesis of 2-hydroxymethyl chromans
KR20040004862A (ko) * 2002-07-05 2004-01-16 한국과학기술연구원 다공성의 비이온성 고분자 흡착제에 고정화된 오스뮴테트록사이드
US20060074149A1 (en) * 2003-09-09 2006-04-06 Boriack Clinton J Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom
US7371875B2 (en) 2004-03-12 2008-05-13 Miikana Therapeutics, Inc. Cytotoxic agents and methods of use
US8765955B2 (en) 2004-06-03 2014-07-01 Brandeis University Asymmetric aldol additions using bifunctional cinchona-alkaloid-based catalysts
US7989647B2 (en) 2005-03-03 2011-08-02 South Dakota Soybean Processors, Llc Polyols derived from a vegetable oil using an oxidation process
KR100812178B1 (ko) * 2006-01-27 2008-03-12 (주)그라쎌 플루오렌기를 함유하는 전기발광화합물 및 이를 발광재료로채용하고 있는 표시소자
CN101759860B (zh) * 2009-11-16 2012-07-25 天津市科迈化工有限公司 球粒状橡胶防老剂fr的生产方法
WO2011159177A1 (fr) 2010-06-18 2011-12-22 Industrial Research Limited Aminohydroxylation améliorée d'alcènes
WO2014148591A1 (fr) * 2013-03-21 2014-09-25 国立大学法人名古屋大学 Procédé de production d'un composé de 1,2-diol
EP3759063A1 (fr) 2018-02-26 2021-01-06 Bischof, Steven M. Synthèse d'alpha-oléfines normales à l'aide d'une déhydroformylation ou d'une déhydroxyméthylation
US20220388931A1 (en) * 2019-11-04 2022-12-08 International Flavors & Fragrances Inc. Dihydroxylation of olefins using osmate (vi) salts
CN112898119A (zh) * 2021-01-27 2021-06-04 宁波南大光电材料有限公司 一种3-羟乙基六氟异丙醇的制备方法及其酸催化装置

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989006225A1 (fr) * 1988-01-11 1989-07-13 Massachusetts Institute Of Technology Dihydroxylation asymetrique catalytique acceleree par un ligand

Family Cites Families (9)

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US4393253A (en) * 1980-11-24 1983-07-12 Exxon Research & Engineering Co. Hydroxylation of olefins
EP0077202B1 (fr) * 1981-10-09 1986-04-09 Exxon Research And Engineering Company Procédé d'hydroxylation d'oléfines utilisant des catalyseurs comprenant un composé osmium-halogène
EP0098701A1 (fr) * 1982-07-01 1984-01-18 Exxon Research And Engineering Company Procédé pour l'hydroxylation des oléfines en présence d'un catalyseur à l'oxyde d'osmium et d'un co-catalyseur au sel d'un acide carboxylique
US4482763A (en) * 1982-07-19 1984-11-13 Exxon Research & Engineering Co. Process for hydroxylating olefins in the presence of an osmium containing catalyst and organic halogenated hydrocarbon co-catalyst
US4496778A (en) * 1983-10-03 1985-01-29 Exxon Research & Engineering Co. Process for the hydroxylation of olefins using molecular oxygen, an osmium containing catalyst, a copper Co-catalyst, and an aromatic amine based promoter
US4496779A (en) * 1984-04-26 1985-01-29 Exxon Research & Engineering Co. Process for the hydroxylation of olefins using molecular oxygen, an osmium containing catalyst, a copper co-catalyst, and a cycloaliphatic amine based promoter
WO1989002428A1 (fr) * 1987-09-18 1989-03-23 Ici Australia Operations Proprietary Limited Procede enantioselectif
US4965364A (en) * 1988-02-23 1990-10-23 Massachusetts Institute Of Technology Ligand-accelerated catalytic asymmetric dihydroxylation
US4871855A (en) 1988-01-11 1989-10-03 Massachusetts Institute Of Technology Ligand-accelerated catalytic asymmetric dihydroxylation using dihydroquinidine and dihydroquinidine esters as ligands

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989006225A1 (fr) * 1988-01-11 1989-07-13 Massachusetts Institute Of Technology Dihydroxylation asymetrique catalytique acceleree par un ligand

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Journal of Organic Chemistry, vol. 55, no. 2, 19 January 1990, Easton (US), M. Makoto et al.: "Osmium tetraoxide catalyzed vicinal hydroxylation of higher olefins by using hexacyanoferrate(III) ion as a cooxidant", pages 766-768, see page 768, lines 15-31 (cited in the application) *
Synthesis, no. 1, January 1989, Stuttgart (DE), G. Cainelli et al.: "Catalytic hydroxalation of olefins by polymer-bound osmium tetroxide", pages 45-47, see the whole article *
Tetrahedron Letters, vol. 31, no. 1, 1990, Oxford (GB), H.-L. Kwong: "Preclusion of the "second Cycle" in the osmium-catalyzed asymmetric dihydroxylation of olefins leads to a superior process", pages 2999-3002, see the whole article (cited in the application) *
Tetrahedron Letters, vol. 31, no. 21, 1990, Oxford (GB), B. Moon Kim et al.: "Heterogeneous catalytic asymmetric dihydroxylation: use of a polymer-bound alkaloid", pages 3003-3006, see the whole article *
Tetrahedron Letters, vol. 31, no. 27, 1990, Oxford (GB) T. Shibata et al.: "Ligand-based improvement of enantioselectivity in the catalytic asymmetric dihydroxylateion of dialkyl substituted olefins", pages 3817-3820, see the whole article (cited in the application) *

Also Published As

Publication number Publication date
CA2081315C (fr) 2004-10-19
CA2081315A1 (fr) 1991-10-24
US5126494A (en) 1992-06-30
EP0526582A1 (fr) 1993-02-10
JP3177244B2 (ja) 2001-06-18
JP3306051B2 (ja) 2002-07-24
JP2001081051A (ja) 2001-03-27
JPH05509297A (ja) 1993-12-22
WO1991016322A2 (fr) 1991-10-31

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