Olefination of ketones using a gold(III)-catalyzed Meyer-Schuster rearrangement.
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.
Engel
Douglas A
DA
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA.
Dudley
Gregory B
GB