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Influence of the Double‐Bond Geometry of the Michael Acceptor on Copper‐Catalyzed Asymmetric Conjugate Addition
Author(s) -
Vuagnouxd'Augustin Magali,
Alexakis Alexandre
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700424
Subject(s) - chemistry , conjugate , copper , nucleophile , steric effects , acceptor , michael reaction , double bond , isomerization , catalysis , reagent , stereochemistry , organic chemistry , mathematical analysis , physics , mathematics , condensed matter physics
Focusing on mechanistic aspects, a study of the influence of the ( E )/( Z ) double‐bond geometry of the Michael acceptor on the enantioselectivity of copper‐catalyzed asymmetric conjugate addition reactions has been realized. In spite of numerous articles concerning copper‐catalyzed asymmetric conjugate addition reactions, the major factors of such a reaction are quite difficult to elucidate. Although our experiments have not allowed us to define strict rules, they have highlighted some factors not to be neglected when considering the approach of the copper reagent to the double bond, such as ( E )/( Z ) isomerization and steric aspects, which could change the reactive conformation of the substrate. Electronic effects could also modify the polarization of the double bond and influence the nucleophilic attack. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)