Synthesis of Enantioenriched 3-Cyclohexene-1-carboxylic Acid via PLE-Catalyzed Desymmetrization and Photo-Driven Hydrodecarboxylation

doi:10.6023/cjoc202511007

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通过猪肝酯酶催化的去对称化反应和光驱动的加氢脱羧反应合成手性3-环己烯-1-羧酸

曹唱^a, 沈超仁^a, 李宗晗^a, 董开武^*,a

^a华东师范大学化学与分子工程学院庄长恭研究所上海市绿色化学与化工过程绿色化重点实验室上海 200062

收稿日期:2025-12-23 修回日期:2026-01-29
基金资助:
国家自然科学基金 (22271094)、国家自然科学基金 (22571086)、上海教育科技创新计划 (2023ZKZD37)、中央高校基础科研项目资助.

Synthesis of Enantioenriched 3-Cyclohexene-1-carboxylic Acid via PLE-Catalyzed Desymmetrization and Photo-Driven Hydrodecarboxylation

Chang Cao^a, Chaoren Shen^a, Zonghan Li^a, Kaiwu Dong^*,a

^aShanghai Key Laboratory of Green Chemistry and Chemical Processes, Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062

Received:2025-12-23 Revised:2026-01-29
Contact: ^*E-mail: kwdong@chem.ecnu.edu.cn
Supported by:
National Natural Science Foundation of China (22271094), the National Natural Science Foundation of China (22571086), the Innovation Program of Shanghai Municipal Education Commission (2023ZKZD37), and the Fundamental Research Funds for the Central Universities. The authors thank Huzhou Yihui Biotechnology Co., Ltd for the courtesy of PLE.

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Abstract

Optically active 3-cyclohexen-1-carboxylic acid is a prevalent structural unit in various pharmaceuticals. Herein, by utilizing porcine liver esterase-catalyzed desymmetrization and light-driven hydrodecarboxylation, an unpresented catalytic asymmetric method for obtaining enantioenriched 3-cyclohexen-1-carboxylic acid from readily available 1,2,3,6-tetrahydrophthalic anhydride was developed. Through experimental and computational investigations, the correlation between the steric hindrance at the 9-position of the acridine photosensitizer and the effect of hydrodecarboxylation of 4-cyclohexene-1,6-dimethanoic acid monomethyl ester was revealed.

Key words: acridine photosensitizer, hydrodecarboxylation, porcine liver esterase

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Chang Cao, Chaoren Shen, Zonghan Li, Kaiwu Dong. Synthesis of Enantioenriched 3-Cyclohexene-1-carboxylic Acid via PLE-Catalyzed Desymmetrization and Photo-Driven Hydrodecarboxylation[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202511007.

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通过猪肝酯酶催化的去对称化反应和光驱动的加氢脱羧反应合成手性3-环己烯-1-羧酸

Synthesis of Enantioenriched 3-Cyclohexene-1-carboxylic Acid via PLE-Catalyzed Desymmetrization and Photo-Driven Hydrodecarboxylation

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