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WO1998027051A3 - Amidohydroxylation asymetrique catalytique d'olefines au moyen de n-halo carboxamides - Google Patents

Amidohydroxylation asymetrique catalytique d'olefines au moyen de n-halo carboxamides Download PDF

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Publication number
WO1998027051A3
WO1998027051A3 PCT/US1997/023511 US9723511W WO9827051A3 WO 1998027051 A3 WO1998027051 A3 WO 1998027051A3 US 9723511 W US9723511 W US 9723511W WO 9827051 A3 WO9827051 A3 WO 9827051A3
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WO
WIPO (PCT)
Prior art keywords
ligands
catalyzed
addition reaction
conditions
amidohydroxylation
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/US1997/023511
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English (en)
Other versions
WO1998027051A2 (fr
WO1998027051A9 (fr
Inventor
K Barry Sharpless
Kyriacos C Nicolaou
Guigen Li
Rodney Guy
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.)
Scripps Research Institute
Original Assignee
Scripps Research Institute
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 Scripps Research Institute filed Critical Scripps Research Institute
Priority to AU57101/98A priority Critical patent/AU5710198A/en
Publication of WO1998027051A2 publication Critical patent/WO1998027051A2/fr
Publication of WO1998027051A3 publication Critical patent/WO1998027051A3/fr
Publication of WO1998027051A9 publication Critical patent/WO1998027051A9/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des β-hydroxyamides synthétisés à partir de substrats d'oléfine au moyen d'une réaction d'addition asymétrique catalytique. Des N-halo carboxamides sont employés en tant que source d'azote oxydante pour la production de β-hydroxysulfonamides. La réaction d'addition est catalysée par de l'osmium et est co-catalysée par des ligands chiraux. Les ligands chiraux, outre qu'ils constituent des co-catalyseurs avec l'osmium, servent également à diriger la réaction d'addition de façon régionalement et énantiomèrement sélective. Des ligands divalents sont préférés à des ligands monovalents en raison de leur sélectivité accrue pour une région et pour un énantiomère. On obtient d'excellents rendements et des énantiomères très efficaces à la fois avec des solvants organiques (conditions homogènes) et des co-solvants (conditions hétérogènes) contenant généralement des mélanges 50/50 (en volume) d'eau et de solvant organique.
PCT/US1997/023511 1996-12-18 1997-12-18 Amidohydroxylation asymetrique catalytique d'olefines au moyen de n-halo carboxamides Ceased WO1998027051A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU57101/98A AU5710198A (en) 1996-12-18 1997-12-18 Catalytic asymmetric amidohydroxylation of olefins with n-halo carboxamides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3313196P 1996-12-18 1996-12-18
US60/033,131 1996-12-18

Publications (3)

Publication Number Publication Date
WO1998027051A2 WO1998027051A2 (fr) 1998-06-25
WO1998027051A3 true WO1998027051A3 (fr) 1998-08-20
WO1998027051A9 WO1998027051A9 (fr) 1998-11-12

Family

ID=21868719

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/023511 Ceased WO1998027051A2 (fr) 1996-12-18 1997-12-18 Amidohydroxylation asymetrique catalytique d'olefines au moyen de n-halo carboxamides

Country Status (2)

Country Link
AU (1) AU5710198A (fr)
WO (1) WO1998027051A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI239327B (en) 2000-03-02 2005-09-11 Upjohn Co Aminohydroxylation of olefins in the presence of acetamide
FR2810666B1 (fr) * 2000-06-22 2002-11-08 Rhodia Chimie Sa Ligands chiraux de type (beta-aminoalkyl)-phosphine, -phosphite, -phosphonite et -phosphinite, complexes metalliques correspondants et leur utilisation dans la catalyse asymetrique
WO2011159177A1 (fr) 2010-06-18 2011-12-22 Industrial Research Limited Aminohydroxylation améliorée d'alcènes

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

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 (4)

* Cited by examiner, † Cited by third party
Title
GUIGEN LI ET AL.: "Catalytic Asymmetric Aminohydroxylation (AA) of Olefins", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 35, no. 4, 1 March 1996 (1996-03-01), WEINHEIM DE, pages 451 - 454, XP002068084 *
HEINRICH BECKER ET AL.: "A New Ligand Class for the Asymmetric Dihydroxylation of Olefins", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 35, no. 4, 1 March 1996 (1996-03-01), WEINHEIM DE, pages 448 - 451, XP002068086 *
K. BARRY SHARPLESS ET AL.: "A New Reaction. Stereospecific Vicinal Oxyamination of Olefins by Alkyl Imido Osmium Compounds", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 97, no. 8, 16 April 1975 (1975-04-16), DC US, pages 2305 - 2307, XP002068085 *
MILAN BRUNCKO ET AL.: "N-Bromoacetamide - A New Nitrogen Source for the Catalytic Asymmetric Aminohydroxylation of Olefins", ANGEWANDTE CHEMIE. INTERNATIONAL EDITION., vol. 36, no. 13/14, 4 August 1997 (1997-08-04), WEINHEIM DE, pages 1483 - 1486, XP002068083 *

Also Published As

Publication number Publication date
WO1998027051A2 (fr) 1998-06-25
AU5710198A (en) 1998-07-15

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