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

Gajendrasingh K. Ingle | Zendy; Michael G. Mormino | Zendy; Jon C. Antilla | Zendy

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

Author(s) -

Gajendrasingh K. Ingle,

Michael G. Mormino,

Jon C. Antilla

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502527q

Subject(s) - desymmetrization , chemistry , epoxide , enantioselective synthesis , nucleophile , catalysis , yield (engineering) , thiol , organic chemistry , phosphate , lithium (medication) , combinatorial chemistry , materials science , metallurgy , medicine , endocrinology

A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting β-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.

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