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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

José M. Concellón* and Eva Bardales

*Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain, Email: jmcguniovi.es

J. M. Concellón, E. Bardales, J. Org. Chem., 2003, 5, 9492-9295.

DOI: 10.1021/jo0349577 (free Supporting Information)


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Abstract

A highly stereoselective synthesis of aromatic α,β-unsaturated amides was achieved by treatment of aromatic α,β-epoxyamides with samarium diiodide. α,β-epoxyamides are easily prepared by the reaction of enolates derived from α-chloroamides with carbonyl compounds at -78°C.



Key Words

epoxyamides, unsaturated amides, reductive elimination, samarium diiodide


ID: J42-Y2003-1080