Synergistic Copper and Chiral Lewis Base Catalysis for the Asymmetric Synthesis of Pyrrolo[1,2-a]indoles,Chinese Journal of Chemistry

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Synergistic Copper and Chiral Lewis Base Catalysis for the Asymmetric Synthesis of Pyrrolo[1,2-a]indoles
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2021-08-25 , DOI: 10.1002/cjoc.202100476
Jia‐Huan Shen ₁ , Fei Tian ₁ , Wu‐Lin Yang ₁ , Wei‐Ping Deng ₁

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The first asymmetric decarboxylative [3+2]-cycloaddition of ethynyl indoloxazolidones with carboxylic acids has been developed under synergistic catalysis of copper and chiral Lewis base. This protocol provides a direct and modular approach to biologically important pyrrolo[1,2-a]indoles bearing two vicinal stereogenic centers with excellent diastereo- and enantioselectivities (up to >20 : 1 dr and >99% ee). In addition, the utility of this methodology was demonstrated by scaled-up reaction and several synthetic transformations of the cycloadduct.

中文翻译：

铜和手性路易斯碱协同催化不对称合成吡咯并[1,2-a]吲哚

在铜和手性路易斯碱的协同催化下，已经开发出乙炔基吲哚恶唑烷酮与羧酸的第一个不对称脱羧 [3+2]-环加成反应。该协议提供了一种直接和模块化的方法来处理生物学上重要的吡咯并 [1,2- a ] 吲哚，这些吲哚带有两个具有出色非对映选择性和对映选择性（高达 >20:1 dr 和 >99% ee）的邻位立体中心。此外，通过放大反应和环加合物的几种合成转化证明了该方法的实用性。

更新日期：2021-08-25

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