Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer

Caroline A. Cheetham, Richard S. Massey, Silvain L. Pira, Robin G. Pritchard, Timothy W. Wallace

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    Abstract

    5-Substituted 6,7-dihydrodibenz[c,e]azepines, a class of secondary amine incorporating a centre-axis chirality relay, are accessible from 1-substituted N-(2-bromobenzyl)-1-phenylmethanamines via N-acylation and ring-closing intramolecular direct arylation. The ring closure proceeds with high atropodiastereoselectivity due to strain effects that are induced by trigonalisation of the nitrogen atom, as predicted using molecular mechanics calculations. © 2011 The Royal Society of Chemistry.
    Original languageEnglish
    Pages (from-to)1831-1838
    Number of pages7
    JournalOrganic and Biomolecular Chemistry
    Volume9
    Issue number6
    DOIs
    Publication statusPublished - 21 Mar 2011

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