Diastereoselective oxidation of substituted 1,2-dithiolan-3-ones

Article abstract of DOI:10.1016/S0040-4039(00)76693-7

Oxidation of 1,2-dithiolan-3-ones 1 with one equivalent of dimethyldioxirane in dichloromethane at -78°C produces the corresponding 1,2-dithiolan-3-one 1-oxides 2 in high yields and with diastereoselectivities as high as 18:1. The major diastereomer formed is the trans isomer. An X-ray crystallographic structure study of the major diastereomer 2c obtained by oxidation of 1g is reported.