Citation: Meng Shan, Yongmei Yu, Mengli Sun, Shuping Yang, Mengqi Wang, Bo Zhu, Junbiao Chang. Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control[J]. Chinese Chemical Letters, ;2025, 36(1): 109781. doi: 10.1016/j.cclet.2024.109781 shu

Bifunctional organocatalyst-catalyzed dynamic kinetic resolution of hemiketals for synthesis of chiral ketals via hydrogen bonding control

State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

zbtiantang@126.com

changjunbiao@zzu.edu.cn

Received Date: 28 November 2023
Revised Date: 3 March 2024
Accepted Date: 14 March 2024
Available Online: 15 March 2024

Figures(4)

Herein, we report the dynamic kinetic resolution asymmetric acylation of γ-hydroxy-γ-perfluoroalkyl butenolides/phthalides catalyzed by amino acid-derived bifunctional organocatalysts, and a series of ketals were obtained in high yields (up to 95%) and excellent enantioselectivities (up to 99%). In terms of synthetic utility, the reaction can be performed on a gram scale, and the product can be converted into potential biological nucleoside analog.
- Bifunctional organocatalyst,
- Dynamic kinetic resolution,
- Hemiketal,
- Chiral ketals,
- Hydrogen bonding
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