Tetrahedron

Vinyl anion equivalent V. Asymmetric synthesis of allylic alcohols using chiral 2-(trialkylsilyl) ethyl sulfoxides

S Kusuda, Y Ueno, T Toru

Index: Kusuda, Shinya; Ueno, Yoshio; Toru, Takeshi Tetrahedron, 1994 , vol. 50, # 4 p. 1045 - 1062

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Citation Number: 28

Abstract

Both enantiomers of optically pure secondary allylic alcohols can be conveniently prepared by the diastereoselective reaction of the α-sulfinyl carbanion of p-tolyl 2-(trialkylsilyl) ethyl sulfoxides or tert-butyl 2-(trimethylsilyl) ethyl sulfoxide with aldehydes followed by either fluoride-induced desilylsulfinylation or thermal elimination of the sulfinyl group.