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Lithium BINOL Phosphate Catalyzed Desymmetrization of meso-Epoxides with Aromatic Thiols

Gajendrasingh Ingle, Michael G. Mormino and Jon C. Antilla*

*Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620, United States, Email: jantillausf.edu

G. Ingle, M. G. Mormino, J. C. Antilla, Org. Lett., 2014, 16, 5548-5551.

DOI: 10.1021/ol502527q (free Supporting Information)



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Abstract

In a highly enantioselective method for desymmetrization of meso-epoxides with aromatic thiols, epoxide activation is achieved using metal BINOL phosphates. β-Hydroxyl sulfides are obtained in excellent yield and enantioselectivity for a broad scope of substrates.

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Key Words

aryl sulfides


ID: J54-Y2014