Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution
3
Shanghai Engineering Center of Industrial Asymmetric Catalysis for Chiral Drugs, Shanghai 200433, China
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Publication type: Journal Article
Publication date: 2023-09-01
scimago Q1
wos Q1
SJR: 1.677
CiteScore: 15.7
Impact factor: 8.9
ISSN: 10018417, 18785964
General Chemistry
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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11
Total citations:
11
Citations from 2024:
9
(81.81%)
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GOST
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Yue X. et al. 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. Vol. 34. No. 9. p. 108178.
GOST all authors (up to 50)
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Yue X., Li Y., Sang D., Yuan T., Huang Z., Chen F. 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. Vol. 34. No. 9. p. 108178.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.cclet.2023.108178
UR - https://doi.org/10.1016/j.cclet.2023.108178
TI - Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution
T2 - Chinese Chemical Letters
AU - Yue, Xiaoping
AU - Li, Yitong
AU - Sang, Di
AU - Yuan, Tao
AU - Huang, Zedu
AU - Chen, Fen-Er
PY - 2023
DA - 2023/09/01
PB - Elsevier
SP - 108178
IS - 9
VL - 34
SN - 1001-8417
SN - 1878-5964
ER -
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BibTex (up to 50 authors)
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@article{2023_Yue,
author = {Xiaoping Yue and Yitong Li and Di Sang and Tao Yuan and Zedu Huang and Fen-Er Chen},
title = {Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution},
journal = {Chinese Chemical Letters},
year = {2023},
volume = {34},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1016/j.cclet.2023.108178},
number = {9},
pages = {108178},
doi = {10.1016/j.cclet.2023.108178}
}
Cite this
MLA
Copy
Yue, Xiaoping, et al. “Asymmetric synthesis of syn-aryl-(2S,3R)-2-chloro-3-hydroxy esters via an engineered ketoreductase-catalyzed dynamic reductive kinetic resolution.” Chinese Chemical Letters, vol. 34, no. 9, Sep. 2023, p. 108178. https://doi.org/10.1016/j.cclet.2023.108178.