STEREOSPECIFIC DISPLACEMENT OF SULFUR FROM CHIRAL CENTERS. ACTIVATION VIA THIAPHOSPHONIUM SALTS.

Article abstract of DOI:10.1016/S0040-4039(00)94972-4

The first general method for direct displacement of sulfur from chiral carbon centers has been developed.Chiral mercaptans are readily converted to the corresponding thiaphosphonium salts by treatment with t-butyl hypochlorite and hexamethylphosphorous triamide.Metathesis with ammonium hexafluorophosphate provides stable, isolable, crystalline salts which undergo clean nucleophilic diplacement with a variety of heteroatom and carbon based nucleophiles, affording products in which the stereochemistry has been inverted.