Atroposelective Synthesis of 3,3’-Bisindoles Bearing Axial and Central Chirality: Using Isatin-Derived Imines as Electrophiles
Atroposelective Synthesis of 3,3’-Bisindoles Bearing Axial and Central Chirality: Using Isatin-Derived Imines as Electrophiles
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具有轴向和中心手性的 3,3-双吲哚的天体选择性合成：使用靛红衍生的亚胺作为亲电子试剂
DOI：
10.1002/cjoc.202000022
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Feng Shi
中科院分区：
文献类型：
--
作者：
Feng-Tao Sheng;Zhi-Min Li;Yi-Zhu Zhang;Li-Xing Sun;Yu-Chen Zhang;Wei Tan;Feng Shi
以吲哚类亚胺为亲电体，通过催化不对称加成反应合成了一类具有轴向和中心手性的新型3，3‘-双吲哚化合物(23例，产率高达80%，>；95：5DR，98：2Er)。该方法利用了手性磷酸催化的2-取代3，3‘-双吲哚的动态动力学拆分，通过这些底物与吲哚亚胺的亲核加成反应。在这种方法中，吲哚类亚胺由于其高反应性和体积大小而成为一类有竞争力的亲电体，这为轴向手性3，3‘-双吲哚与一个具有重要生物学意义的手性3-氨基氧吲哚单元的结合提供了一种容易的途径。这种方法极大地扩展了动态动力学拆分策略在合成同时具有轴向手性和中心手性的3，3‘-双吲哚对映体的通用性和适用性。
An atroposelective synthesis of a new class of 3,3’-bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin-derived imines as electrophiles (23 examples, up to 80% yield, > 95 : 5 dr, 98 : 2 er). This approach takes advantage of chiral phosphoric acid-catalyzed dynamic kinetic resolution of 2-substituted 3,3’-bisindoles via nucleophilic addition of such substrates with isatin-derived imines. In this approach, isatin-derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size, which provided an easy access to axially chiral 3,3'-bisindoles incorporated with a biologically important chiral 3-aminooxindole unit. This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3’-bisindole derivatives bearing both axial and central chirality.