Regiodivergent Kinetic Resolution of Terminal and Internal rac-Aziridines with Malonates under Dinuclear Schiff Base Catalysis

Regiodivergent parallel kinetic resolution of aziridines with malonates was achieved under dinuclear Schiff base catalysis. The regiodivergent reaction proceeded under catalyst-control irrespective of the substituents on the aziridines, and 2.5-10 mol % of a Y(OTf)3/La(OiPr)3/a dinucleating Schiff base = 1:1:1 mixture gave versatile γ-amino acid derivatives in 96 → >99.5% ee. Not only terminal but also internal racemic aziridines reacted smoothly under suitably combined Lewis acid/Brønsted base catalysis.