Issue 6, 2011
From the journal:

Organic & Biomolecular Chemistry

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

Caroline A. Cheetham,a   Richard S. Massey,a   Silvain L. Pira,a   Robin G. Pritcharda  and  Timothy W. Wallace*a  

* Corresponding authors

a School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK
E-mail: tim.wallace@manchester.ac.uk
Fax: +44 (0) 161 275 4939

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.

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

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Article information

DOI
https://doi.org/10.1039/C0OB00889C
Article type
Paper
Submitted
16 Oct 2010
Accepted
10 Dec 2010
First published
26 Jan 2011

Org. Biomol. Chem., 2011,9, 1831-1838

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

C. A. Cheetham, R. S. Massey, S. L. Pira, R. G. Pritchard and T. W. Wallace, Org. Biomol. Chem., 2011, 9, 1831 DOI: 10.1039/C0OB00889C

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