Efficient Direct Synthesis of Aziridine‐Containing Chiral Tridentate Ligands by the Iminium‐Mediated Self‐Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes.

An efficient method for the direct synthesis of aziridine‐containing chiral tridentate ligands was developed from enantiopure aziridines and salicylaldehydes. The method achieved the regiospecific cleavage of more substituted C−N bonds of aziridines through an iminium‐mediated self‐ring opening reaction of aziridines with up to 95% yield and complete inversion of configuration. The (S)‐2‐alkylaziridine‐derived tridentate ligands displayed excellent activity and stereoselectivity in the zinc trifluoromethanesulfonate‐catalyzed asymmetric aldol reactions of acetone and aromatic aldehydes. [ABSTRACT FROM AUTHOR]