Base-induced heterochiral dimerization of an oxiranyl carbaldimine: Stereoselective synthesis of a highly functionalized aziridine

Treatment of the oxiranyl carbaldimine with base (LDA or LDA/KOtBu) leads i n an one-step procedure to the polyfunctionalized aziridine, This highly di astereoselective reaction is explained by a new type of an Aza-Darzens reac tion, in which one enantiomer of the starting material is deprotonated to f orm an oxiranyl anion, which attacks the imine carbon atom of the other ena ntiomer (mutual kinetic resolution by double diastereofacial selection).