Asymmetric Synthesis of Spiro[Azetidine-3,3′-Indoline]-2,2′-Diones via Copper(I)-Catalyzed Kinugasa/C−C Coupling Cascade Reaction,Angewandte Chemie International Edition

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Asymmetric Synthesis of Spiro[Azetidine-3,3′-Indoline]-2,2′-Diones via Copper(I)-Catalyzed Kinugasa/C−C Coupling Cascade Reaction
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2022-09-02 , DOI: 10.1002/anie.202208323
Xianqiang Zhong ₁ , Meirong Huang ₂ , Huilan Xiong ₁ , Yuzhen Liang ₁ , Wei Zhou ₁ , Qian Cai ₁

Affiliation

Spiro[azetidine-indolines] are important scaffolds in diversified bioactive compounds, but asymmetric synthesis of chiral spiro[azetidine-3,3′-indolines] remains unexplored. In this work, a copper-catalyzed asymmetric Kinugasa/C−C coupling cascade reaction of N-(2-iodo-aryl)-propiolamides with nitrones has been developed, affording chiral spiro[azetidine-3,3′-indoline]-2,2′-diones as single diastereomers with high yields and good enantioselectivity.

中文翻译：

螺[Azetidine-3,3'-Indoline]-2,2'-Diones 通过铜 (I)-催化的 Kinugasa/C−C 偶联级联反应的不对称合成

螺[azetidine-indolines] 是多种生物活性化合物的重要支架，但手性螺[azetidine-3,3'-indolines] 的不对称合成仍未探索。在这项工作中，开发了N -(2-iodo-aryl)-propiolamides 与硝酮的铜催化不对称 Kinugasa/CC 偶联级联反应，提供手性螺 [azetidine-3,3'-indoline]-2 ,2'-二酮作为单一非对映体，具有高产率和良好的对映选择性。

更新日期：2022-09-02

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