Direct Aziridination of Nitroalkenes Affording N-Alkyl-C-nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β-Nitroenamines.

A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.