Stereoselective synthesis of [formula omitted]- and [formula omitted]-1,2-diols from diketo sulfides via [formula omitted]-3,4-dihydroxythiolanes

Abstract

Intramolecular reductive coupling reaction of a series of diketo sulfides ( 1 ) by a low-valent titanium reagent at 0 °C in tetrahydrofuran leads to cis -3,4-dihydroxythiolanes ( 2 ) exclusively in 67–89% yields. Desulfurization of 2 by Raney nickel in ethanol affords either erythro - or or threo -1,2-diols ( 3 ) in 51–82% yields.