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:
jmcg
uniovi.es
J. M. Concellón, E. Bardales, J. Org. Chem., 2003, 5, 9492-9295.
DOI: 10.1021/jo0349577
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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
