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Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.

ABSTRACT: 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 ?-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.

SUBMITTER: Ingle G

PROVIDER: S-EPMC4227545 | biostudies-literature | 2014 Nov

REPOSITORIES: biostudies-literature

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Lithium BINOL phosphate catalyzed desymmetrization of meso-epoxides with aromatic thiols.

Ingle Gajendrasingh G Mormino Michael G MG Antilla Jon C JC

Organic letters 20141015 21

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. ...[more]

PMID: 25317934

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