Zhang Qing-Qing, Jin Fei, Yu Jun-Hui, Zhang Chuang, Zhang Mao, Deng Ming-Zhenlong, Lin Shu-Xian, Chen Lei, Zhao Yong-Long, He Bin, Li Yan
State Key Laboratory of Functions and Applications of Medicinal Plants, Engineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Provincial Key Laboratory of Pharmaceutics, School of Pharmacy, Guizhou Medical University, Guiyang 550004, China.
J Org Chem. 2024 Jul 19;89(14):10099-10111. doi: 10.1021/acs.joc.4c00956. Epub 2024 Jun 29.
This article explores the asymmetric Michael addition reaction of 2-hydroxy-1,4-naphthoquinone and indole-3-ones catalyzed by cinchona alkaloids. This strategy utilizes 2-hydroxy-1,4-naphthoquinone and easily prepared indole-3-one as substrates, resulting in the synthesis of 23 unprecedented indolin-3-ones bearing a 1,4-naphthoquinone unit at the C2 position of indole under simple and mild reaction conditions, with up to 88% yield, 98% , and >20:1 .
本文探讨了金鸡纳生物碱催化的2-羟基-1,4-萘醌与吲哚-3-酮的不对称迈克尔加成反应。该策略以2-羟基-1,4-萘醌和易于制备的吲哚-3-酮为底物，在简单温和的反应条件下，合成了23种前所未有的在吲哚C2位带有1,4-萘醌单元的吲哚啉-3-酮，产率高达88%，ee值为98%，dr值>20:1。
