Synlett 2004(8): 1431-1433  
DOI: 10.1055/s-2004-829095
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Synthesis of α-Branched Enones

David A. Kummer, Jehrod B. Brenneman, Stephen F. Martin*
Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712, USA
Fax: +1(512)4714180; e-Mail: sfmartin@mail.utexas.edu;
Further Information

Publication History

Received 11 March 2004
Publication Date:
22 June 2004 (online)

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Abstract

A new method for preparing α-branched enones from carboxylic acid derivatives is reported. The procedure commenced by the reaction of N,O-dimethylamides with a masked acyl anion equivalent, followed by the addition of (trimethylsilyl-methyl)cerium dichloride to give intermediates that undergo Lewis acid mediated olefination to produce enol ethers that are then hydrolyzed to afford simple α-branched enones in high overall yields.