Catalytic Asymmetric Kinetic Resolution of 2,2-Disubstituted Styrenyl Aziridines via Ring Opening with Amines

We report herein the activation of racemic 2,2-disubstituted styrenyl aziridines by Lewis acid catalysis to undergo ring-opening reactions at a tertiary carbocenter via kinetic resolution with amines. A range of chiral diamine products bearing α-tertiary stereogenic centers as well as enantioenriched aziridines were obtained in good to high yields and enantioselectivities. The synthetic utility of the reaction was demonstrated in various product elaborations, including the synthesis of NK₁ antagonist SCH388714.