Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement |
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Authors: | Engel Douglas A Dudley Gregory B |
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Affiliation: | Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA. |
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Abstract: | An atom-economical and efficient olefination strategy for ketones is described. Ethoxyacetylide addition followed by a gold-catalyzed Meyer-Schuster rearrangement affords alpha,beta-unsaturated esters, generally in excellent overall yield from the starting ketones. The alkynophilicity of Au3+ promotes an interaction with the electron-rich acetylenes that catalyzes the Meyer-Schuster rearrangement selectively over other conceivable pathways. |
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