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Origin of the Minor Enantiomeric Product in a Noyori Asymmetric Hydrogenation: Evidence for Pathways Different to the Major Mechanism
Author(s) -
Ishibashi Yoshitaka,
Bessho Yuhki,
Yoshimura Masahiro,
Tsukamoto Masaki,
Kitamura Masato
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502463
Subject(s) - mechanism (biology) , enantiomer , chemistry , asymmetric hydrogenation , enantioselective synthesis , noyori asymmetric hydrogenation , stereochemistry , organic chemistry , catalysis , physics , quantum mechanics
Hidden pathways : The enantiomeric products of the catalytic hydrogenation of an isotopically labeled substrate were separated. The ratios of the isotopomers revealed that the major and minor enantiomers are formed mostly through different mechanisms. Hence, when analyzing the energy profile of an asymmetric catalytic reaction with the Arrhenius equation, two competing diastereomorphic catalytic cycles should be considered (see scheme).