Tetrahedron Letters p. 4867 - 4870 (1985)
Update date:2022-08-11
Topics:
Krafft, Grant A.
Siddall, Thomas L.
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.
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