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Updated: Jun 5, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality
Caroline A Cheetham1, Richard S Massey, Silvain L Pira
1School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK M13 9PL.
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.
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