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

作者：Cheetham Caroline A; Massey Richard S; Pira Silvain L; Pritchard Robin G; Wallace Timothy W^*

来源：Organic and Biomolecular Chemistry, 2011, 9(6): 1831-1838.

DOI：10.1039/c0ob00889c

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.

• 出版日期2011