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

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Direct Aziridination of Nitroalkenes Affording N-Alkyl-C-nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β-Nitroenamines
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-21 00:00:00 , DOI: 10.1021/acs.orglett.7b02724
Feiyue Hao ₁ , Haruyasu Asahara ₁ , Nagatoshi Nishiwaki ₁

Affiliation

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.

中文翻译：

得到硝基烯烃的直接氮杂环丙烷ñ -烷基- Ç -nitroaziridines和随后的路易斯酸介导的异构化，以β-Nitroenamines

的温和和高度非对映一锅合成反式- ñ -烷基- Ç -nitroaziridines是通过用脂族胺和硝基烯烃的实现Ñ氯琥珀酰亚胺。用路易斯酸处理所获得的氮丙啶类化合物导致容易的开环反应，伴随着重排和异构化为官能化的（Z）-β-亚硝胺。

更新日期：2017-09-21

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