Zirconium-Catalyzed Enantioselective Ring Opening of meso-Aziridines

Significance

Optically active 1,2-diamines are commonly found in natural products, organocatalysts, ligands, resolving agents, and chiral auxiliaries. One increasingly important method for their synthesis is by ring opening of meso-aziridines. Significant progress in this transformation has been previously made by the authors utilizing ­early-transition-metal catalysis. In this report, meso-aziridines bearing an N-benzhydryl group are opened by aniline derivatives using a zirconium(IV) catalyst in the presence of a tridentate binol ligand. The protecting group can be removed by hydrogenolysis to give the monoamine-free ­diamine.