硝基亚乙烯的直接氮丙啶化生成 N-烷基-C-硝基氮丙啶，以及随后的路易斯酸介导的异构化为β-硝基烯胺。
Direct Aziridination of Nitroalkenes Affording N-Alkyl-C-nitroaziridines and the Subsequent Lewis Acid Mediated Isomerization to β-Nitroenamines.
机构信息
School of Environmental Science and Engineering, and ‡Research Center for Material Science and Engineering, Kochi University of Technology , Tosayamada, Kami, Kochi 782-8502, Japan.
出版信息
Org Lett. 2017 Oct 6;19(19):5442-5445. doi: 10.1021/acs.orglett.7b02724. Epub 2017 Sep 21.
PMID:28933166
Abstract
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.
摘要
通过硝基烯烃与脂肪胺和 N-氯代丁二酰亚胺的一锅法温和高非对映选择性反应，可制备反式 N-烷基-C-硝基氮丙啶。用路易斯酸处理得到的氮丙啶可发生开环反应，同时发生重排和异构化，生成功能化的（Z）-β-硝基烯胺。
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