Enantioselective Synthesis of Atropisomeric Biaryls by Pd-Catalyzed Asymmetric Buchwald–Hartwig Amination,Angewandte Chemie International Edition

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Enantioselective Synthesis of Atropisomeric Biaryls by Pd-Catalyzed Asymmetric Buchwald–Hartwig Amination
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-08-09 , DOI: 10.1002/anie.202108747
Peng Zhang ₁ , Xiao-Mei Wang ₁ , Qi Xu ₁ , Chang-Qiu Guo ₁ , Peng Wang ₁ , Chuan-Jun Lu ₁ , Ren-Rong Liu ₁

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N−C Biaryl atropisomers are prevalent in natural products and bioactive drug molecules. However, the enantioselective synthesis of such molecules has not developed significantly. Particularly, the enantioselective synthesis of N−C biaryl atropisomers by stereoselective metal-catalyzed aryl amination remains unprecedented. Herein, a Pd-catalyzed cross-coupling strategy is presented for the synthesis of N−C axially chiral biaryl molecules. A broad spectrum of N−C axially chiral compounds was obtained with excellent enantioselectivities (up to 99 % ee) and good yields (up to 98 %). The practicality of this reaction was validated in the synthesis of useful biological molecules.

中文翻译：

通过 Pd 催化的不对称 Buchwald-Hartwig 胺化反应对映选择性合成阻转异构联芳基化合物

NC 联芳基阻转异构体普遍存在于天然产物和生物活性药物分子中。然而，此类分子的对映选择性合成尚未显着发展。特别是，通过立体选择性金属催化芳基胺化反应对映选择性合成 NC 联芳基阻转异构体仍然是前所未有的。在此，提出了一种用于合成 NC 轴向手性联芳基分子的 Pd 催化交叉偶联策略。获得了广谱的 NC 轴向手性化合物，具有出色的对映选择性（高达 99 % ee）和良好的产率（高达 98 %）。该反应的实用性在有用的生物分子的合成中得到验证。

更新日期：2021-09-20

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