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An Easy, Efficient, and Completely Stereoselective Synthesis of (E)-α,β-Unsaturated Esters via Sequential Aldol-Type/Elimination Reactions Promoted by Samarium Diiodide or Chromium Dichloride

José M. Concellón,* Carmen Concellón and Carmen Méjica

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

J. M. Concellón, C. Concellón, C. Méjica, J. Org. Chem., 2005, 70, 6111-6113.

DOI: 10.1021/jo050655o (free Supporting Information)


The stereoselective reaction of different aldehydes and ethyl dibromoacetate promoted by SmI2 or CrCl2 gives (E)-α,β-unsaturated esters by an an aldol-type reaction and a subsequent β-elimination reaction.

see article for more examples

The First Sequential Reaction Promoted by Manganese: Complete Stereoselective Synthesis of (E)-α,β-Unsaturated Esters from 2,2-Dichloroesters and Aldehydes

J. M. Concellón, H. Rodríquez-Solla, P. Díaz, R. Llaona, J. Org. Chem., 2007, 72, 4396-4400.

Key Words

Samarium Diiodide, Chlorium Dichloride, α,β-Unsaturated Esters

ID: J42-Y2005-940