Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer.
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.
School of Chemistry, The University of Manchester, Oxford Road, Manchester, UK M13 9PL.
Caroline A
CA
Cheetham
Richard S
RS
Massey
Silvain L
SL
Pira
Robin G
RG
Pritchard
Timothy W
TW
Wallace