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: jmcg
uniovi.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
ID: J54-Y2007-2240
