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The First Cyclopropanation Reaction of Unmasked α,β-Unsaturated Carboxylic Acids: Direct and Complete Stereospecific Synthesis of Cyclopropanecarboxylic Acids Promoted by Sm/CHI3

José M. Concellón,* Humberto Rodríguez-Solla and Carmen Simal

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

J. M. Concellón, H. Rodríguez-Solla, C. Simal, Org. Lett., 2007, 9, 2685-2688.

DOI: 10.1021/ol0709174 (free Supporting Information)


Abstract

A samarium-promoted cyclopropanation can be carried out on unmasked (E)- or (Z)-α,β-unsaturated carboxylic acids. In all cases the process is completely stereospecific and stereoselective. A mechanism has been proposed.


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Key Words

Cyclopropanes, Samarium


ID: J54-Y2007-2240