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■ Stereoselective Synthesis of Hexahydro-1,4-thiazepin-3-one and Dihydro-1,4-thiazin-3-one Derivatives

Michinori Karikomi, Tohru Yamazaki, Yukiko Abematsu, Kiyoshi Masuzawa, and Takashi Toda*

*Department of Applied Chemistry, Faculty of Engineering, Utsunomiya University, 7-1-2 Yoto, Utsunomiya 321-8585, Japan

Abstract

Diastereomerically pure 4-benzyl-7-substituted 6-hydroxyhexahydro-1,4-thiazepin-3-one and 4-benzyl-1’-hydroxyalkyl-1,4-tetrahydrothiazin-3-one derivatives are obtained by the reaction of a 2,3-epoxy alkylamine derivative with methyl thioglycolate in good yields. trans-Epoxy amine derivatives gave trans-thiazepinone derivatives and anti-thiazepinone derivatives whilst cis-epoxy amines gave cis-thiazepinone and syn-thiazepinone derivatives. Substituent effects on regioselectivity were also examined with the use of several epoxy amine derivatives.