Bulletin of the Chemical Society of Japan

Alcoholysis of Epoxides Catalyzed by Tetracyanoethylene and Dicyanoketene Acetals.

Y Masaki, T Miura, M Ochiai

Index: Masaki, Yukio; Miura, Tsuyoshi; Ochiai, Masahito Bulletin of the Chemical Society of Japan, 1996 , vol. 69, # 1 p. 195 - 205

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Citation Number: 47

Abstract

A typical π-acid tetracyanoethylene and capto-dative olefin dicyanoketene acetals were found to catalyze stereospecific alcoholysis of epoxides at the ambient temperature to 50° C in good yields. Mildness and significant chemoselectivity of the catalysts were demonstrated by intactness of tetrahydropyranyl ether and ethylene acetal groups. A novel regioselectivity associated with anchimeric assistance of the ethereal group on the side chain was ...