ol7b02724_si_001.pdf (2.8 MB)
Direct Aziridination of Nitroalkenes Affording N‑Alkyl‑C‑nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β‑Nitroenamines
journal contribution
posted on 2017-09-20, 22:03 authored by Feiyue Hao, Haruyasu Asahara, Nagatoshi NishiwakiA 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.