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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

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José M. Concellón,* Carmen Concellón, and Carmen Méjica

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

J. Org. Chem., 2005, 70 (15), pp 6111–6113

DOI: 10.1021/jo050655o

Publication Date (Web): June 25, 2005

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

(E)-α,β-Unsaturated esters can be obtained with complete stereoselectivity by reaction of different aldehydes and ethyl dibromoacetate promoted by SmI₂ or CrCl₂. The transformation takes place as two sequential reactions: an aldol-type reaction and a β-elimination reaction.

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Published In Issue July 22, 2005
Received April 4, 2005

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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