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Paper | Regular issue | Vol 51, No. 1, 1999, pp.85-94
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8353
Oxazepines and Thiazepines, 36. Diastereoselective Sulfoxidation of 2,3-Dihydro-1,5-benzothiazepin-4(5H)-ones by Dimethyldioxirane

Tamás Patonay,* Waldemar Adam,* József Jeko, Katalin E. Kövér, Albert Lévai, Márta Németh, and Karl Peters

*Department of Organic Chemistry, Lajos Kossuth University, H-4010 Debrecen, P.O.Box 20, Hungary

Abstract

The highly chemoselective dimethyldioxirane oxidation of 2-substituted 2,3-dihydro-1,5-benzothiazepin-4(5H)-one (1) allows the synthesis of the corresponding sulfoxides (2) or sulfones (3) in good yields. The relative stereochemistry of the sulfoxides has been unequivocally determined by X-Ray and NMR methods. The high trans diastereoselectivity can be explained on the basis of steric control.