Synlett 2007(6): 0949-0953  
DOI: 10.1055/s-2007-973885
LETTER
© Georg Thieme Verlag Stuttgart · New York

The Meyer-Schuster Rearrangement of Ethoxyalkynyl Carbinols

Susana S. Lopez, Douglas A. Engel, Gregory B. Dudley*
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA
Fax: +1(850)6448281; e-Mail: gdudley@chem.fsu.edu;
Further Information

Publication History

Received 15 January 2007
Publication Date:
26 March 2007 (online)

Zoom Image

Abstract

The combination of electron-rich alkoxyacetylenes and cationic gold catalysts provides excellent reactivity for the Meyer-Schuster rearrangement under mild conditions. Optimization of the reaction conditions with respect to stereoselectivity and investigations into the scope and mechanism of the rearrangement of secondary ethoxyalkynyl carbinols (γ-ethoxy-substituted propargyl alcohols) to α,β-unsaturated esters are described.