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

被引：9

作者：

Hao, Feiyue ^{[1
]}

Asahara, Haruyasu ^{[1
,2
,3
]}

Nishiwaki, Nagatoshi ^{[1
,2
]}

机构：

[1] Kochi Univ Technol, Sch Environm Sci & Engn, Kochi 7828502, Japan

[2] Kochi Univ Technol, Res Ctr Mat Sci & Engn, Kochi 7828502, Japan

[3] Osaka Univ, Dept Appl Chem, Fac Engn, Yamadaoka 2-1, Suita, Osaka 5650871, Japan

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 19期

关键词：

STEREOSELECTIVE-SYNTHESIS; ALDEHYDES; 1,4-DIHYDROPYRIDINES; CONSTRUCTION; CYCLIZATION; 1,3-DIPOLE; LITHIATION; ACCESS;

D O I：

10.1021/acs.orglett.7b02724

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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)-beta-nitroenamines.

引用

页码：5442 / 5445

页数：4

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