Citation: 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. doi: 10.6023/cjoc201911027 shu

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

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

Corresponding author: Liu Yaozong,
Received Date: 23 November 2019
Revised Date: 4 January 2020
Available Online: 15 January 2020

Figures(2)

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.
- asymmetric catalysis,
- bifunctional thiourea,
- Michael addition,
- 1-acetylindolin-3-one,
- β, γ-unsaturated α-keto ester
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沈阳化工大学材料科学与工程学院沈阳 110142