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

José M. Concellón* and Carmen Concellón

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

J. M. Concellon, C. Concellon, J. Org. Chem., 2006, 71, 1728-1731.

DOI: 10.1021/jo052236x

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Abstract

The stereoselective reaction of different aldehydes and dibromoacetic acid promoted by SmI₂ gives (E)-α,β-unsaturated carboxylic acids. The mechanism is discussed.

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Key Words

Samarium Diiodide, Unsaturated Carboxylic Acids

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ID: J42-Y2006-450