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Enantioselective Synthesis of 2‐Aryl Cyclopentanones by Asymmetric Epoxidation and Epoxide Rearrangement
Author(s) -
Shen YuMei,
Wang Bin,
Shi Yian
Publication year - 2006
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.200501520
Subject(s) - enantioselective synthesis , epoxide , aryl , ketone , lewis acids and bases , chemistry , catalysis , enantiomer , enantiomeric excess , chiral lewis acid , organic chemistry , stereochemistry , alkyl
Optically active epoxides are prepared by the highly enantioselective epoxidation of benzylidenecyclobutanes using a glucose‐derived ketone as the catalyst and oxone as the oxidant. A subsequent Lewis acid catalyzed rearrangement of the resulting epoxides with Et 2 AlCl or LiI provides α‐aryl substituted cyclopentanones in high enantiomeric excess (see scheme; Tol= tolyl).
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