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

doi:10.6023/cjoc201911027

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

双官能团硫脲催化吲哚-3-酮对β,γ-不饱和酮酯的不对称Michael加成反应研究

刘耀宗^a, 许鹏飞^b, 马建军^a, 李晓明^a, 梁睿渊^a, 滕志君^a

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 E-mail:1048632722@qq.com

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

Liu Yaozong^a, Xu Pengfei^b, Ma Jianjun^a, Li Xiaoming^a, Liang Ruiyuan^a, Teng Zhijun^a

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

1. 201378S.pdf(2035KB)

Abstract

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

Cite this article

Liu Yaozong, Xu Pengfei, Ma Jianjun, Li Xiaoming, Liang Ruiyuan, Teng Zhijun. Bifunctional Thioureas Catalyzed Asymmetric Michael Addition of 1-Acetylindolin-3-ones to β,γ-Unsaturated α-Keto Esters[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1378-1383.

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双官能团硫脲催化吲哚-3-酮对β,γ-不饱和酮酯的不对称Michael加成反应研究

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

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