REGIOSPECIFIC ALLYLATION OF SULFUR SUBSTITUTED ACTIVE METHYLENE COMPOUNDS WITH ALLYLIC BROMIDES

Abstract Allylation sulfur substituted active methylene compounds such as RSCH2Y [Y = C(=O)R, COOR, CN] with allylic bromides in the presence of bases gives a mixture of the SN2-product and the apparent SN2′-product. The former product is selectively obtained in alkylation in a nonpolar solvent. Synthetic utility of this regiospecific allylation is demonstrated in the simple synthesis of pellitorine.