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  • Title: 2,2- and 2,6-Diarylpiperidines by aryl migration within lithiated urea derivatives of tetrahydropyridines.
    Author: Tait MB, Butterworth S, Clayden J.
    Journal: Org Lett; 2015 Mar 06; 17(5):1236-9. PubMed ID: 25692395.
    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.
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