Copper-Catalyzed Cyanoalkylative Aziridination of N-Sulfonyl Allylamines

被引：8
|
作者：
Ha, Tu M. [1 ]
Guo, Weisi [1 ]
Wang, Qian [1 ]
Zhu, Jieping [1 ]
机构：
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Synth & Nat Prod, EPFL SB ISIC LSPN, BCH 5304, CH-1015 Lausanne, Switzerland
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 11期
关键词：
aziridine; alkyl nitrile; radical; alkene; homogeneous catalysis; copper; C(SP(3))-H BOND FUNCTIONALIZATION; ACTIVATED ALKENES; ALLYLIC ALCOHOLS; ALKYL NITRILES; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED ALKENES; CYANOMETHYLATION; ACETONITRILE; EPOXIDES; OLEFINS;
D O I：
10.1002/adsc.202000276
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Reaction of N-arylsulfonyl allylamines with alkyl nitriles in the presence of di-tert-butyl peroxide (DTBP) and a catalytic amount of copper salt afforded homologated aziridines in 43-86% yield. A sequence involving addition of the in situ generated cyanomethyl radical to the double bond followed by a copper-mediated intramolecular C-N bond formation accounted for the reaction outcome. 2,3-Disubstituted allylamines were converted to trisubstituted aziridines in a stereoselective manner. Starting from enantioenriched allylamines, chiral aziridines were obtained diastereoselectively.
引用
收藏
页码：2205 / 2210
页数：6
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