Tetrahedron letters

The practical procedure for a preparation of 1-chloroalkyl p-tolyl sulfoxides in high optically active form: A very short synthesis of optically active disparlure

T Satoh, T Oohara, Y Ueda, K Yamakawa

Index: Satoh, Tsuyoshi; Oohara, Teruhiko; Ueda, Yoshiko; Yamakawa, Koji Tetrahedron Letters, 1988 , vol. 29, # 3 p. 313 - 316

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Citation Number: 64

Abstract

Abstract A chlorination of optically active alkyl p-tolyl sulfoxides with N-chlorosuccinimide in dichloromethane in the presence of potassium carbonate afforded optically active 1- chloroalkyl p-tolyl sulfoxides in 87–94% ee (88–94% chemical yields). The optically active chloroalkyl sulfoxide was applied to a synthesis of optically active (+)-disparlure.