STEREOCONTROLLED ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE ACYLCYCLOPROPANE DERIVATIVES BY MICHAEL ADDITIONS OF BROMOMALONATE TO CHIRAL α-ACYLVINYLIC SULFOXIDES

Abstract

Michael addition of bromomalonate carbanions to chiral α-acylvinylic sulfoxides and the subsequent intramoleculer alkylation yielded optically active acylcyclopropane derivatives with high enantiomeric excess. Stereochemistry of the product was determined by chemical correlation to a compound of known absolute configuration. The mechanism for the asymmetric induction is deduced on the basis of the stereochemical results obtained.