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Direct Reaction of Dibromoacetic Acid with Aldehydes Promoted by Samarium Diiodide: An Easy, Efficient, and Rapid Synthesis of (E)-α,β-Unsaturated Carboxylic Acids with Total Stereoselectivity^†

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José M. Concellón* and Carmen Concellón

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., 2006, 71 (4), pp 1728–1731

DOI: 10.1021/jo052236x

Publication Date (Web): January 20, 2006

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

A promoted SmI₂ direct reaction of dibromoacetic acid with different aldehydes, followed by an elimination reaction also promoted by samarium diiodide, affords (E)-α,β-unsaturated carboxylic acids 2 with total stereoselectivity. A mechanism to explain this transformation is proposed.

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Published In Issue February 17, 2006
Received October 27, 2005

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Note

Direct Reaction of Dibromoacetic Acid with Aldehydes Promoted by Samarium Diiodide: An Easy, Efficient, and Rapid Synthesis of (E)-α,β-Unsaturated Carboxylic Acids with Total Stereoselectivity^†