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

作者:Mino Takashi*; Yamada Haruka; Komatsu Shingo; Kasai Mizuki; Sakamoto Masami; Fujita Tsutomu
来源:European Journal of Organic Chemistry, 2011, (24): 4540-4542.
DOI:10.1002/ejoc.201100769

摘要

Acyclic amines 1 were obtained by a nucleophilic aromatic substitution (SNAr) 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 la 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).

  • 出版日期2011-8