Atropisomerism at C-N bonds of acyclic amines: Synthesis and application to palladium-catalyzed asymmetric allylic alkylations

摘要

Acyclic amines 1 were obtained by a nucleophilic aromatic substitution (S_NAr) reaction and N-methylation followed by silane reduction. The optical resolution of C (aryl)-N (amine) bond atropisomers of amines 1 is described. We found that chiral acyclic amine 1a can be resolved by crystallization without any outside chiral source. Finally, we demonstrate the ability of chiral amines 1 as a ligand in a palladium-catalyzed asymmetric allylic alkylation (up to 93% ee).