. alpha.,. beta.-Epoxy sulfoxides as useful intermediates in organic synthesis. 21. A novel approach to the asymmetric synthesis of epoxides, allylic alcohols,. alpha.- …

…, T Oohara, Y Ueda, K Yamakawa

Index: Satoh, Tsuyoshi; Oohara, Teruhiko; Ueda, Yoshiko; Yamakawa, Koji Journal of Organic Chemistry, 1989 , vol. 54, # 13 p. 3130 - 3136

Full Text: HTML

Citation Number: 2

Abstract

A practical and relatively inexpensive procedure for the preparation of (-)-chloromethyl p- tolyl sulfoxide of high optical purity was accomplished by the chlorination of optically pure (+)- methyl p-tolyl sulfoxide with N-chlorosuccinimide in the presence of K2C03. The (-)- chloromethyl p-tolyl sulfoxide was alkylated to give a diastereomeric mixture of (-)-1- chloroalkyl p-tolyl sulfoxides. Addition of the anion derived from these sulfoxides to ...