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Phosphorothioic Acids and Related Compounds as Surrogates for H2S-Synthesis of Chiral Tetrahydrothiophenes

Forest J. Robertson and Jimmy Wu*

*Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, United States, Email: jimmy.wudartmouth.edu

F. J. Robertson, J. Wu, J. Am. Chem. Soc., 2012, 134, 2775-2780.

DOI: 10.1021/ja210758n (free Supporting Information)


Abstract

A convenient preparation of chiral tetrahydrothiophenes (THTs) in high enantiopurity via phosphorothioic acids circumvents the use of H2S which is a highly toxic gas. The key transformation is a base-promoted, intramolecular, highly stereospecific carbon-sulfur bond-forming event through a double SN2 displacement mechanism. The methodology is amenable to a broad array of functional groups and heterocycles.

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Key Words

Corey-Bakshi-Shibata Reduction, tetrahydrothiophenes


ID: J48-Y2012-0350