Copper‐Catalyzed Cyanoalkylative Aziridination of N‐Sulfonyl Allylamines,Advanced Synthesis & Catalysis

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Copper‐Catalyzed Cyanoalkylative Aziridination of N‐Sulfonyl Allylamines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-03-23 , DOI: 10.1002/adsc.202000276
Tu M. Ha ₁ , Weisi Guo ₁ , Qian Wang ₁ , Jieping Zhu ₁

Affiliation

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.

中文翻译：

铜催化的N-磺酰基烯丙基胺的氰烷基化叠氮化

在过氧化二叔丁基（DTBP）和催化量的铜盐存在下，N-芳基磺酰基烯丙基胺与烷基腈的反应提供了均相的氮丙啶，收率为43-86％。反应结果涉及一个序列，该序列涉及将原位生成的氰基甲基自由基添加到双键中，然后形成铜介导的分子内CN键。2,3-二取代的烯丙胺以立体选择性方式转化为三取代的氮丙啶。从对映体富集的烯丙胺开始，非对映选择性地获得手性氮丙啶。

更新日期：2020-03-23

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