Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

Abstract

Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes β-elimination of its C-2 substituent. © Wiley-VCH Verlag GmbH & Co. KGaA, 2008.