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

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

https://doi.org/10.6023/cjoc201911027

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.