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

✍ Scribed by Takashi Mino; Haruka Yamada; Shingo Komatsu; Mizuki Kasai; Masami Sakamoto; Tsutomu Fujita

Publisher: John Wiley and Sons
Year: 2011
Tongue: English
Weight: 278 KB
Volume: 2011
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.201100769

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✦ Synopsis

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).

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