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Synthesis of Aromatic (E)- or (Z)-α,β-Unsaturated Amides with Total or Very High Selectivity from α,β-Epoxyamides and Samarium Diiodide

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José M. Concellón* and Eva Bardales

Departamento de Qumica Orgnica e Inorgnica, Facultad de Qumica, Universidad de Oviedo, Julin Clavera, 8, 33071 Oviedo, Spain jmcg@sauron.quimica.uniovi.es

J. Org. Chem., 2003, 68 (24), pp 9492–9495

DOI: 10.1021/jo0349577

Publication Date (Web): October 28, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Highly stereoselective synthesis of aromatic α,β-unsaturated amides was achieved by treatment of aromatic α,β-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from α-chloroamides with carbonyl compounds at −78 °C. A mechanism to explain this transformation is proposed.

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