Stereospecific displacement of sulfur from chiral centers. activation via thiaphosphonium salts

Autor: Thomas L. Siddall, Grant A. Krafft
Rok vydání: 1985
Předmět:
Zdroj: Tetrahedron Letters. 26:4867-4870
ISSN: 0040-4039
Popis: 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.
Databáze: OpenAIRE