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Organolithium/Chiral Lewis Base/BF 3 : a Versatile Combination for the Enantioselective Desymmetrization of meso ‐Epoxides
Author(s) -
Vrancken Emmanuel,
Alexakis Alexandre,
Mangeney Pierre
Publication year - 2005
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.200400745
Subject(s) - enantioselective synthesis , desymmetrization , lewis acids and bases , chemistry , nucleophile , base (topology) , ring (chemistry) , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , mathematics , mathematical analysis
Abstract BF 3 can be used in combination with organolithium/strong Lewis base complexes for the enantioselective nucleophilic ring‐opening or the carbenoidic rearrangement of various meso ‐oxiranes with excellent yields and ee values of up to 87 %. Mechanistic aspects of these reactions are considered. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)