STEREOSELECTIVE SYNTHESIS OF HEXAHYDRO-1,4-THIAZEPIN-3-ONE AND DIHYDRO-1,4-THIAZIN-3-ONE DERIVATIVES

Diastereomerically pure 4-benzyl-7-substituted 6-hydroxy-hexahydro-1,4 -thiazepin-3-one and enzyl-1'-hydroxyalkyl-1,4-tetra-hydrothiazin-3-on e derivatives are obtained by the reaction of a 2,3-epoxy alkylamine d erivative 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-thia zepinone derivatives. Substituent effects on regioselectivity were als o examined with the use of several epoxy amine derivatives.