Olefination of Ketones Using a Gold(III)-catalyzed Meyer-Schuster Rearrangement

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2006 Aug 25

PMID 16928065

Citations 11

Authors

Douglas A Engel

Gregory B Dudley

Affiliations

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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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