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Mechanism and Stereoselectivity of Asymmetric Hydrogenation

Rhodium complexes containing chiral phosphine ligands catalyze the hydrogenation of olefinic substrates such as α-aminoacrylic acid derivatives, producing chiral products with very high optical yields. Elucidation of the mechanisms of such reactions leads to the conclusion that the stereoselection i... Full description

Journal Title: Science 30 July 1982, Vol.217(4558), pp.401-407
Main Author: Halpern, Jack
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: ISSN: 00368075 ; E-ISSN: 10959203
Link: https://www.jstor.org/stable/1689149
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recordid: jstor_archive_231689149
title: Mechanism and Stereoselectivity of Asymmetric Hydrogenation
format: Article
creator:
  • Halpern, Jack
subjects:
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical reactions
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical properties
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Physics -- Mechanics
  • Physical sciences -- Physics -- Microphysics
  • Physical sciences -- Chemistry -- Chemical compounds
  • Physical sciences -- Chemistry -- Chemical reactions
ispartof: Science, 30 July 1982, Vol.217(4558), pp.401-407
description: Rhodium complexes containing chiral phosphine ligands catalyze the hydrogenation of olefinic substrates such as α-aminoacrylic acid derivatives, producing chiral products with very high optical yields. Elucidation of the mechanisms of such reactions leads to the conclusion that the stereoselection is dictated not by the preferred initial binding of the substrate to the chiral catalyst, but rather by the much higher reactivity of the minor diastereomer of the catalyst-substrate adduct corresponding to the less favored binding mode.
language: eng
source:
identifier: ISSN: 00368075 ; E-ISSN: 10959203
fulltext: fulltext
issn:
  • 0036-8075
  • 00368075
  • 1095-9203
  • 10959203
url: Link


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subjectPhysical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical reactions ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical properties ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Physics -- Mechanics ; Physical sciences -- Physics -- Microphysics ; Physical sciences -- Chemistry -- Chemical compounds ; Physical sciences -- Chemistry -- Chemical reactions
descriptionRhodium complexes containing chiral phosphine ligands catalyze the hydrogenation of olefinic substrates such as α-aminoacrylic acid derivatives, producing chiral products with very high optical yields. Elucidation of the mechanisms of such reactions leads to the conclusion that the stereoselection is dictated not by the preferred initial binding of the substrate to the chiral catalyst, but rather by the much higher reactivity of the minor diastereomer of the catalyst-substrate adduct corresponding to the less favored binding mode.
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titleMechanism and Stereoselectivity of Asymmetric Hydrogenation
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abstractRhodium complexes containing chiral phosphine ligands catalyze the hydrogenation of olefinic substrates such as α-aminoacrylic acid derivatives, producing chiral products with very high optical yields. Elucidation of the mechanisms of such reactions leads to the conclusion that the stereoselection is dictated not by the preferred initial binding of the substrate to the chiral catalyst, but rather by the much higher reactivity of the minor diastereomer of the catalyst-substrate adduct corresponding to the less favored binding mode.
pubThe American Association for the Advancement of Science
doi10.1126/science.217.4558.401
date1982-07-30