A novel synthesis of 1,3-diol diesters by the reaction of aldehydes with oxime esters catalyzed by samarium complex

Article abstract of DOI:10.1246/cl.1998.53

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.