Stereoselective cyclization of alkyl N-phthaloyl-4-bromoglutamates to cyclopropane derivatives

The kinetics of the reactions of alkyl N-phthaloyl-4-bromoglutamates with Et3N and KOH was investigated. The reactions proceed stereospecifically to form alkyl 1-phthalimidocyclopropane-r-1,t-2-dicarboxylates. In alcohols, the reactions are accompanied by transesterification. The concerted mechanism accounting for the stereospecificity of these reactions is proposed.