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.
|Number of pages||7|
|Journal||Organic and Biomolecular Chemistry|
|Publication status||Published - 21 Mar 2011|
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CCDC 793197: Experimental Crystal Structure Determination
Cheetham, C. A. (Contributor), Massey, R. S. (Contributor), Pira, S. L. (Contributor), Pritchard, R. (Contributor) & Wallace, T. (Contributor), Cambridge Crystallographic Data Centre, 1 Jan 2011
DOI: 10.5517/ccvmd0v, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccvmd0v&sid=DataCite