Chiral Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution of 3-Hydroxyphthalides for Enantioselective Synthesis of Phthalidyl Esters
Zeyang Hao
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
Search for more papers by this authorWei Lin
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
Search for more papers by this authorZi-Qi Yuan
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
Search for more papers by this authorCorresponding Author
Wei Zhang
West China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu, Sichuan, 610041 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Xin Li
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
E-mail: [email protected]; [email protected]Search for more papers by this authorZeyang Hao
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
Search for more papers by this authorWei Lin
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
Search for more papers by this authorZi-Qi Yuan
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
Search for more papers by this authorCorresponding Author
Wei Zhang
West China School of Public Health and West China Fourth Hospital, Sichuan University, Chengdu, Sichuan, 610041 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Xin Li
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China; Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Phthalides serve as core structures pervasive in a wide array of natural products and drug molecules, which display a diverse array of biological activities. We report herein a highly efficient dynamic kinetic resolution of 3-hydroxyphthalides by chiral isothioureas (ITUs) catalyzed asymmetric acylation, facilitating the effective synthesis of a variety of chiral phthalidyl esters with good yields and enantioselectivities. Notably, this reaction features mild reaction conditions, expansive substrate scope as well as good functional group compatibility. In addition, the practicality of this method is underscored by the large-scale synthesis, reduced catalyst loading experiment and the synthesis of the chiral phthalidyl ester prodrug.
Supporting Information
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Appendix S1: Supporting Information |
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