Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis

• Jingran Tao,
• Li-Mei Jin and
• X. Peter Zhang

Beilstein J. Org. Chem. 2014, 10, 1282–1289, doi:10.3762/bjoc.10.129

• ; cobalt complex; metalloradical catalysis; organophosphorus; phosphoryl azide; Introduction Aziridines, the smallest three-membered nitrogen-containing heterocycles, are highly valuable heterocyclic compounds that are widely used in organic synthesis and pharmaceuticals [1][2]. As a result, tremendous

• radical intermediate [29][30][31][32][33][34]. It is worthy to note the importance of dual functions of the chiral amide units of the D2-symmetric chiral amidoporphyrin ligands played in the Co(II)-based metalloradical catalysis (MRC): the rigid amide spacers do not only support and orient the chiral

• metalloradical catalysis (MRC). (A) Potential H-bonding interaction in postulated nitrene radical complex of [Co(D2-Por*)]. R* represents a chiral unit. (B) Geometry corresponding to the minimum energy from simplified computer modeling by molecular mechanics with Spartan 10. The P=O…H–N distance of (1.87 Å