Direct Aziridination of Nitroalkenes Affording N‑Alkyl‑C‑nitroaziridines
and the Subsequent Lewis Acid Mediated Isomerization to β‑Nitroenamines
Posted on 2017-09-20 - 22:03
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.
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Hao, Feiyue; Asahara, Haruyasu; Nishiwaki, Nagatoshi (2017). Direct Aziridination of Nitroalkenes Affording N‑Alkyl‑C‑nitroaziridines
and the Subsequent Lewis Acid Mediated Isomerization to β‑Nitroenamines. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b02724
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