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Asymmetric Epoxidation of Enones With Oxygen in the Presence of Diethylzinc and ( R,R )‐ N ‐Methylpseudoephedrine
Author(s) -
Enders Dieter,
Zhu Jiqun,
Raabe Gerhard
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199617251
Subject(s) - diethylzinc , enantiomeric excess , chemistry , enantiomer , oxygen , alcohol , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis
An efficient method for the asymmetric epoxidation of α,β‐unsaturated ketones 1 is embodied in their reaction with oxygen in the presence of diethylzinc and ( R,R )‐ N ‐methyl‐pseudoephedrine. It affords epoxides 2 in excellent yields, with complete diastereoselectivity, and with enantiomeric excesses of up to 92% ee . The enantiomerically pure amino alcohol employed can be recovered virtually quantitatively with unchanged optical purity.