Memory of Chirality (MOC) Concept in Imino-Aldol Reaction: Enantioselective Synthesis of α,β-Diamino Esters and Aziridines

A simple strategy for the synthesis of chiral α,β-diamino- and α-amino,β-hydroxy ester derivatives in high yields with moderate to high ee has been developed via asymmetric imino-aldol and aldol reactions, respectively, starting from protected aminoesters employing memory of chirality concept for chiral induction. This strategy has been extended for the enantioselective synthesis of aziridines (ee up to 92%). The absolute configuration of the imino-aldol adducts has been determined. The stereochemical outcome of the products has been explained by a suitable mechanism and supported by computational studies.