The first cyclopropanation reaction of unmasked alpha,beta-unsaturated carboxylic acids: direct and complete stereospecific synthesis of cyclopropanecarboxylic acids promoted by Sm/CHI3.
A samarium-promoted cyclopropanation of unmasked alpha,beta-unsaturated acids is described. This reaction can be carried out on (E)- or (Z)-alpha,beta-unsaturated carboxylic acids. In all cases the process is completely stereospecific and stereoselective. A mechanism has been proposed to explain the cyclopropanation reaction.
Concellón
José M
JM
Departamento de Química OrgAnica e InorgAnica, Universidad de Oviedo, Julián Clavería 8, 33071 Oviedo, Spain. jmcg@uniovi.es
Rodríguez-Solla
Humberto
H
Simal
Carmen
C