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

页码：2205 / 2210

页数：6

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