Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1378-1383.DOI: 10.6023/cjoc201911027 Previous Articles     Next Articles


刘耀宗a, 许鹏飞b, 马建军a, 李晓明a, 梁睿渊a, 滕志君a   

  1. a 甘肃银光聚银化工有限公司 甘肃白银 730900;
    b 兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000
  • 收稿日期:2019-11-23 修回日期:2020-01-04 发布日期:2020-01-15
  • 通讯作者: 刘耀宗

Bifunctional Thioureas Catalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β,γ-Unsaturated α-Keto Esters

Liu Yaozonga, Xu Pengfeib, Ma Jianjuna, Li Xiaominga, Liang Ruiyuana, Teng Zhijuna   

  1. a Gansu Yinguang Juyin Chemical Co., Ltd., Baiyin, Gansu 730900;
    b State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000
  • Received:2019-11-23 Revised:2020-01-04 Published:2020-01-15

The asymmetric Michael addition of 1-acetylindolin-3-ones to β,γ-unsaturated α-keto esters catalyzed by bifunctional thioureas has been developed. Enantio-pure 2-substituted indolin-3-one derivatives were obtained easily in excellent yields (up to 99%) with good diastereoselectivity (up to 10:1) and excellent enantioselectivities (up to 99.5%), which would be useful for the chiral synthesis of indole-related compounds.

Key words: asymmetric catalysis, bifunctional thiourea, Michael addition, 1-acetylindolin-3-one, β,γ-unsaturated α-keto ester