Atropisomerism at C-N Bonds of Acyclic Amines: Synthesis and Application to Palladium-Catalyzed Asymmetric Allylic Alkylations
Atropisomerism at C-N Bonds of Acyclic Amines: Synthesis and Application to Palladium-Catalyzed Asymmetric Allylic Alkylations
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无环胺 C-N 键的阻转异构现象：钯催化不对称烯丙基烷基化的合成及其应用
DOI：
10.1002/ejoc.201100769
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发表时间：
2011
期刊：
影响因子：
--
通讯作者：
and Tsutomu Fujita
中科院分区：
文献类型：
--
作者：
Takashi Mino;Haruka Yamada;ShingoKomatsu;Mizuki Kasai;Masami Sakamoto;and Tsutomu Fujita
无环胺1是通过亲核芳香取代（SNAr）反应和N-甲基化然后硅烷还原得到的。描述了胺的 C（芳基）-N（胺）键阻转异构体的光学拆分。我们发现手性无环胺1a可以通过结晶拆分，无需任何外部手性源。最后，我们证明了手性胺作为配体在钯催化的不对称烯丙基烷基化反应中的能力（高达 93%ee）。
Acyclic amines1were obtained by a nucleophilic aromatic substitution (SNAr) reaction andN‐methylation followed by silane reduction. The optical resolution of C(aryl)–N(amine) bond atropisomers of amines1is described. We found that chiral acyclic amine1acan be resolved by crystallization without any outside chiral source. Finally, we demonstrate the ability of chiral amines1as a ligand in a palladium‐catalyzed asymmetric allylic alkylation (up to 93 %ee).