Domino Reaction of Pyrrolidinium Ylides: Michael Addition/[1,2]-Stevens Rearrangement,The Journal of Organic Chemistry

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Domino Reaction of Pyrrolidinium Ylides: Michael Addition/[1,2]-Stevens Rearrangement
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-03-13 00:00:00 , DOI: 10.1021/acs.joc.7b03278
Anna Kowalkowska ₁ , Andrzej Jończyk ₁ , Jan K. Maurin _{2,

3}

Affiliation

A novel domino reaction featuring a Michael addition/[1,2]-Stevens rearrangement reaction of pyrrolidinium ylides with electrophilic alkenes is described. Ylides generated under mild conditions from 2-aryl-N-cyanomethyl-N-methylpyrrolidinium salts entered the Michael addition, followed by a [1,3]-hydrogen shift and finally the [1,2]-Stevens rearrangement to give 3-aryl-2-cyano-2-(2-EWG-ethyl)-1-methylpiperidines.

中文翻译：

吡咯烷鎓叶立德的多米诺反应：迈克尔加成/ [1,2]-史蒂文斯重排

描述了一种新颖的多米诺骨牌反应，其特征在于吡咯烷鎓烷基化物与亲电子烯烃的迈克尔加成/ [1,2]-史蒂文斯重排反应。在温和条件下由2-芳基-N-氰甲基-N-甲基吡咯烷鎓盐生成的叶立德进入Michael加成反应，随后发生[1,3]-氢转移，最后发生[1,2] -Stevens重排，得到3-芳基-2-氰基-2-（2-EWG-乙基）-1-甲基哌啶。

更新日期：2018-03-13

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