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WO1998027051A3 - Catalytic asymmetric amidohydroxylation of olefins with n-halo carboxamides - Google Patents

Catalytic asymmetric amidohydroxylation of olefins with 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
Authority
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
Other languages
French (fr)
Other versions
WO1998027051A2 (en
WO1998027051A9 (en
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/en
Publication of WO1998027051A3 publication Critical patent/WO1998027051A3/en
Publication of WO1998027051A9 publication Critical patent/WO1998027051A9/en
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

β-Hydroxyamides are synthesized from olefin substrates by means of a catalyzed asymmetric addition reaction. N-halo carboxamides are employed as the oxidant nitrogen source for the production of the β-hydroxysulfonamides. The addition reaction is catalyzed by osmium and is co-catalyzed by chiral ligands. The chiral ligands, in addition to being co-catalysts with the osmium, also serve to direct the addition reaction regioselectively and enantio-selectively. Divalent ligands are preferred over monovalent ligands because of their enhanced regio- and enantio-selectivity. Excellent yields and enantiomeric efficiencies are achieved with both organic solvents (homogeneous conditions) and co-solvent conditions (heterogenous conditions), generally containing a 50/50 (v/v) mixtures of water and organic solvent.
PCT/US1997/023511 1996-12-18 1997-12-18 Catalytic asymmetric amidohydroxylation of olefins with n-halo carboxamides Ceased WO1998027051A2 (en)

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 (en) 1998-06-25
WO1998027051A3 true WO1998027051A3 (en) 1998-08-20
WO1998027051A9 WO1998027051A9 (en) 1998-11-12

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1997/023511 Ceased WO1998027051A2 (en) 1996-12-18 1997-12-18 Catalytic asymmetric amidohydroxylation of olefins with n-halo carboxamides

Country Status (2)

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AU (1) AU5710198A (en)
WO (1) WO1998027051A2 (en)

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 (en) * 2000-06-22 2002-11-08 Rhodia Chimie Sa CHIRAL LIGANDS OF THE BETA-AMINOALKYL TYPE -PHOSPHIN, -PHOSPHITE, -PHOSPHONITE AND -PHOSPHINITE, CORRESPONDING METAL COMPLEXES AND THEIR USE IN ASYMMETRIC CATALYSIS
WO2011159177A1 (en) 2010-06-18 2011-12-22 Industrial Research Limited Improved aminohydroxylation of alkenes

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989006225A1 (en) * 1988-01-11 1989-07-13 Massachusetts Institute Of Technology Ligand-accelerated catalytic asymmetric dihydroxylation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989006225A1 (en) * 1988-01-11 1989-07-13 Massachusetts Institute Of Technology Ligand-accelerated catalytic asymmetric dihydroxylation

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 (en) 1998-06-25
AU5710198A (en) 1998-07-15

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