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Marked Deuterium Isotope Effects on the Enantioselectivity in Rhodium‐Catalyzed Asymmetric Hydrogenation of Enamides
Author(s) -
Imamoto Tsuneo,
Itoh Takuma,
Yoshida Kazuhiro,
Gridnev Ilya D.
Publication year - 2008
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200800146
Subject(s) - kinetic isotope effect , deuterium , chemistry , rhodium , catalysis , substituent , asymmetric hydrogenation , aryl , catalytic cycle , isotope , hydrogen , medicinal chemistry , enantioselective synthesis , organic chemistry , alkyl , physics , quantum mechanics
Deuterium isotope effects on the enantioselectivity in the rhodium‐catalyzed asymmetric hydrogenation of enamides and related substrates have been studied. Distinct deuterium isotope effects were observed in the hydrogenation of aryl‐substituted enamides having an ortho substituent that is capable of forming a hydrogen bond. The observed isotope effects are interpreted in terms of the competitive reactions of two dihydride intermediates and dideuteride intermediates that exist in equilibrium in the catalytic cycle.