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

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journal contribution
posted on 2018-03-13, 14:23 authored by Anna Kowalkowska, Andrzej Jończyk, Jan K. Maurin
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.

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