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Carbonylation of epoxides to substituted 3-hydroxy-delta-lactones.

ABSTRACT: Substituted 3-hydroxy-delta-lactones (3HLs) are valuable intermediates in the synthesis of pharmaceuticals and other biologically active natural products. Herein we report the first example of the catalytic carbonylation of substituted homoglycidols to 3HLs using HCo(CO)4. Upon optimization of the catalyst and reaction conditions, a functionally diverse set of 3HLs was prepared. Mechanistic insight was gained by observation of the carbonylation reaction using in situ IR spectroscopy, and we propose a mechanism that is consistent with previously studied epoxide carbonylation systems.

SUBMITTER: Kramer JW

PROVIDER: S-EPMC2596996 | biostudies-literature | 2007 Dec

REPOSITORIES: biostudies-literature

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Carbonylation of epoxides to substituted 3-hydroxy-delta-lactones.

Kramer John W JW Joh Daniel Y DY Coates Geoffrey W GW

Organic letters 20071121 26

Substituted 3-hydroxy-delta-lactones (3HLs) are valuable intermediates in the synthesis of pharmaceuticals and other biologically active natural products. Herein we report the first example of the catalytic carbonylation of substituted homoglycidols to 3HLs using HCo(CO)4. Upon optimization of the catalyst and reaction conditions, a functionally diverse set of 3HLs was prepared. Mechanistic insight was gained by observation of the carbonylation reaction using in situ IR spectroscopy, and we prop ...[more]

PMID: 18027958

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