Bulletin of the Chemical Society of Japan

Asymmetric trasformation of symmetrical epoxides to allylic alcohols by lithium (S)-2-(N, N-disubstituted aminomethyl) pyrrolidide

M Asami

Index: Asami Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 3 p. 721 - 727

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Citation Number: 120

Abstract

Enantioselective deprotonation of symmetrical epoxides was studied by using chiral lithium amide, prepared from (S)-2-(N, N-disubstituted aminomethyl) pyrrolidine and butyllithium. Chiral allylic alcohols were obtained with moderate to high enantiomeric excesses (ee's)(41– 92% ee) from several cyclic and acyclic epoxides employing lithium (S)-2-(1- pyrrolidinylmethyl) pyrrolidide in tetrahydrofuran (THF) in the presence of 1, 8- ...