Synthesis of C-N Axially Chiral N-Arylbenzo[g]indoles via a Central-to-Axial Chirality Conversion Strategy.

Abstract

Gold-catalyzed cascade cyclization of diynes for the synthesis of previously unexplored C-N axially chiral N-arylbenzo[g]indoles was described. The transformation was achieved via a central-to-axial chirality conversion strategy. The chiral conversion exhibited high efficiency. Besides single C-N chiral axis, N-arylbenzo[g]indoles bearing both C-N and C-C chiral axes were also afforded. The title compound derived monophosphine ligand was prepared and was evaluated in Pd-catalyzed asymmetric allylic substitutions, showing excellent chiral induction ability.