文献类型：期刊文献

英文题名：Synthesis of Indole-Fused Eight-Membered Oxa-Rings via Palladium-Catalyzed Asymmetric [4+4] Cycloaddition of Indole-2,3-Quinodimethanes with 2-Alkylidenetrimethylene Carbonates

作者：Lu, Xinhao[1];Wang, Yi[2];He, Chenghan[3];Liu, Yang-Zi[1];Deng, Wei-Ping[1,2]

机构：[1]Zhejiang Normal Univ, Coll Chem & Mat Sci, Key Lab Minist Educ Adv Catalysis Mat, Jinhua 321004, Zhejiang, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Frontiers Sci Ctr Optogenet Tech Cell Met, Sch Pharm, Shanghai 200237, Peoples R China;[3]Chinese Univ Hong Kong, Sch Sci & Engn, Shenzhen 518172, Guangdong, Peoples R China

年份：2024

卷号：42

期号：24

起止页码：3393

外文期刊名：CHINESE JOURNAL OF CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:001312854600001)，CCR-EXPANDED(收录号:WOS:001312854600001)】；

基金：We are grateful for financial support from the Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang (2022R01007), the NSFC (22171082, 22201253), the Start-up Research Grant from Zhejiang Normal University, and the Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism.

语种：英文

外文关键词：Pd-catalyzed; Asymmetric [4+4] cycloaddition; Indole-2,3-quinodimethanes; 2-Alkylidenetrimethylene carbonates; Indole-fused eight-membered oxa-rings

摘要：We report a palladium-catalyzed asymmetric [4+4] cycloaddition reaction between 2-alkylidenetrimethylene carbonate and electron-deficient indole-2,3-quinodimethanes (IQDMs). This reaction features exclusive regioselectivity, high yield (up to 98%), excellent enantioselectivity (up to 95% ee), and easy scale-up without any loss of efficiency, making it valuable for the synthesis of indole-fused eight-membered oxa-rings. The Pd-catalyzed asymmetric [4+4] cycloaddition reaction between 2-alkylidenetrimethylene carbonate and electron-deficient indole-2,3-quinodimethanes (IQDMs) results in the formation of indole-fused eight-membered oxa-rings with high enantioselectivity and excellent yield (up to 98% yield, 95% ee). The practicality of the method is evidenced by the successful gram-scale reaction and efficient product transformation. image