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Synthesis 2009(15): 2523-2530  
DOI: 10.1055/s-0029-1216869
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Efficient Synthesis of trans-β,γ-Unsaturated α-Keto Amides

Christophe Allais, Thierry Constantieux*, Jean Rodriguez*
Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille, CNRS UMR 6263 iSm2, Centre Saint Jérôme - service 531, 13397 Marseille Cedex 20, France
Fax: +33(4)91289187; e-Mail: thierry.constantieux@univ-cezanne.fr; e-Mail: jean.rodriguez@univ-cezanne.fr;
Further Information

Publication History

Received 7 April 2009
Publication Date:
26 June 2009 (online)

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Abstract

A highly efficient, metal-free, and selective access to trans-β,γ-unsaturated α-keto amides is described via peptidic coupling, involving easy to prepare trans-β,γ-unsaturated α-keto acids and commercially available amines.

Key words

β,γ-unsaturated α-keto amide - α-keto acid - amine - peptidic coupling - Michael acceptor

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Purity was superior to 95%, as estimated by NMR analysis.