A Novel Synthesis of 1,3-Diol Diesters by the Reaction of Aldehydes with Oxime Esters Catalyzed by Samarium Complex

Abstract

Abstract CP*2Sm(thf)2 was found to be an efficient catalyst for the synthesis of 1,3-diol diesters by the coupling reaction of aldehydes with oxime esters under mild conditions. For instance, the reaction of acetaldehyde with cyclohexanone oxime acetate catalyzed by CP*2Sm(thf)2 gave 1,3-diacetoxybutane in 70% yield. Treatment of acetaldehyde with isopropenyl acetate in the presence of a small amount of cyclohexanone oxime acetate and Cp*2Sm(thf)2 resulted in the corresponding 1,3-diol diester in good yield.