2,2- and 2,6-Diarylpiperidines by Aryl Migration within Lithiated Urea Derivatives of Tetrahydropyridines

Michael B. Tait, Sam Butterworth, Jonathan Clayden

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    Abstract

    2-Aryltetrahydropyridines formed by anionic cyclization or ring-closing metathesis were converted to their N′-aryl urea derivatives. Depending on the position of the unsaturation within the tetrahydropyridine ring, metalation by deprotonative lithiation or carbolithiation led to migration of the N′-aryl substituent to the 2- or 6-position via intramolecular nucleophilic attack of a benzylic organolithium on the aryl ring. The products are a range of 2,2-, 2,2,3-, and 2,6-polysubstituted piperidine derivatives. Related chemistry was observed in pyrroline homologues.
    Original languageEnglish
    Pages (from-to)1236-1239
    Number of pages3
    JournalOrganic Letters
    Volume17
    Issue number5
    DOIs
    Publication statusPublished - 18 Feb 2015

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