Indole-based atropisomers have emerged as an important backbone in drug discovery and novel catalyst/ligand design. However, the development of asymmetric synthesis of axially chiral 2-arylindoles is sluggish due to their very low rotation barrier. Herein, we developed an amine-catalyzed atroposelective F–C alkylation of rotation-free 2-arylindoles with α,β-unsaturated aldehydes via the DKR process. Various axially chiral 2-arylindoles were obtained with good results. Besides, a promising chiral phosphine was derived from the obtained atropisomers.

中文翻译：

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一种催化性萎缩选择性 Friedel-Crafts 烷基化反应，通过动态动力学分辨率获得轴向手性 C2-芳吲哚


基于吲哚的促异构体已成为药物发现和新型催化剂/配体设计的重要支柱。然而，由于轴向手性 2-芳吲哚的旋转势垒非常低，因此轴向手性 2-芳吲哚的不对称合成的发展缓慢。在此，我们通过 DKR 工艺开发了一种胺催化的无旋转 2-芳吲哚与 α，β-不饱和醛的无旋选择性 F-C 烷基化。获得了各种轴向手性 2-芳吲哚，结果良好。此外，从获得的促性异构体衍生出一种有前途的手性膦。