- Atroposelective formation of dibenz[c,e]azepines via intramolecular direct arylation with centre-axis chirality transfer
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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.
- Cheetham, Caroline A.,Massey, Richard S.,Pira, Silvain L.,Pritchard, Robin G.,Wallace, Timothy W.
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p. 1831 - 1838
(2011/04/26)
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