Organic letters

Olefination of ketones using a gold (III)-catalyzed Meyer-Schuster rearrangement

DA Engel, GB Dudley

Index: Engel, Douglas A.; Dudley, Gregory B. Organic Letters, 2006 , vol. 8, # 18 p. 4027 - 4029

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Citation Number: 146

Abstract

An atom-economical and efficient olefination strategy for ketones is described. Ethoxyacetylide addition followed by a gold-catalyzed Meyer-Schuster rearrangement affords α, β-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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