Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution
Chinese Chemical Letters(2023)
Abstract
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.
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Key words
asymmetric synthesis,syn-aryl,ketoreductase-catalyzed
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