Citation: Xiaoping Yue, Yitong Li, Di Sang, Yuan Tao, Zedu Huang, Fener Chen. Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution[J]. Chinese Chemical Letters, ;2023, 34(9): 108178. doi: 10.1016/j.cclet.2023.108178 shu

Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution

Xiaoping Yue ^a ,
Yitong Li ^a ,
Di Sang ^{b, c} ,
Yuan Tao ^{b, c} ,
Zedu Huang ^{b, c, *,} ,
Fener Chen ^{a, b, c, *,}

a.
Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
b.
Engineering Center of Catalysis and Synthesis for Chiral Molecules, Department of Chemistry, Fudan University, Shanghai 200433, China
c.
Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China

huangzedu@fudan.edu.cn

rfchen@fudan.edu.cn

Received Date: 5 December 2022
Revised Date: 16 January 2023
Accepted Date: 29 January 2023
Available Online: 31 January 2023

Figures(4)

We report here a generic, green synthesis of 17 valuable syn-aryl-(2S,3R)-2–chloro-3–hydroxy esters (syn-(2S,3R)-1) in 73%-99% isolated yields along with 6.1:1–83:1 dr and 31%~ > 99% ee, through dynamic reductive kinetic resolution of racemic aryl α–chloro β-keto esters (2) catalyzed by an engineered ketoreductase which was obtained via epPCR-based directed evolution. The hectogram scale synthesis of syn-(2S,3R)-1b at a substrate concentration of 120 g/L showcased the application potential of the biocatalytic method developed presently.
- (2S,3R)-2-Chloro-3-hydroxy esters,
- Dynamic reductive kinetic resolution,
- Ketoreductase,
- Directed evolution,
- Asymmetric synthesis
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