Lithium benzenetellurolate-induced Reformatsky-type reaction in the presence of cerium trichloride

Abstract

Reformatsky-type reactions with PhTeLi in the presence of CeCl₃ proceeded smoothly under mild conditions. The PhTeLi–CeCl₃ reagent was particularly efficient for the reactions of sterically hindered and enolizable ketones; in the absence of CeCl₃ unsatisfactory yields of the desired β-hydroxy ketone were obtained. It is assumed that CeCl₃ reactions involve a cerium enolate intermediate. The stereoselectivity of the reaction between ethyl 2-bromopropionate and benzaldehyde is also described.