Lithiation of Cinnamyl Chloride: Stereoselective Synthesis of Propargylic Oxiranes and Aziridines

Propargylic oxiranes 4a−e and aziridines 8a−c have been prepared from cinnamyl chloride through lithiation−alkylation with α-halo carbonyl compounds and α-chloro imines, respectively. The reaction with substituted α-halo carbonyl compounds and α-chloro imines proved to be highly E diastereoselective.