Synthesis of aromatic (E)- or (Z)-alpha,beta-unsaturated amides with total or very high selectivity from alpha,beta-epoxyamides and samarium diiodide |
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| Authors: | Concellón José M Bardales Eva |
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| Institution: | Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Julián Clavería, 8, 33071 Oviedo, Spain. jmcg@sauron.quimica.uniovi.es |
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| Abstract: | Highly stereoselective synthesis of aromatic alpha,beta-unsaturated amides was achieved by treatment of aromatic alpha,beta-epoxyamides with samarium diiodide. The starting compounds 1 and 3 are easily prepared by the reaction of enolates derived from alpha-chloroamides with carbonyl compounds at -78 degrees C. A mechanism to explain this transformation is proposed. |
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