Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 6, Pages 1831-1838Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00889c
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- University of Manchester
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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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