Atropisomerism at C–N Bonds of Acyclic Amines: Synthesis and Application to Palladium‐Catalyzed Asymmetric Allylic Alkylations

Abstract

Abstract Acyclic amines 1 were obtained by a nucleophilic aromatic substitution (S N Ar) 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 ).