Chiral Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution of 3-Hydroxyphthalides for Enantioselective Synthesis of Phthalidyl Esters
Zeyang Hao , Wei Lin , Zi-Qi Yuan , Wei Zhang , Xin Li
Chinese Journal of Chemistry ›› 2024, Vol. 42 ›› Issue (19) : 2341 -2345.
Chiral Isothiourea-Catalyzed Acylative Dynamic Kinetic Resolution of 3-Hydroxyphthalides for Enantioselective Synthesis of Phthalidyl Esters
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.
Asymmetric catalysis / Phthalidyl ester / Dynamic kinetic resolution / Chiral isothiourea / Acylation / Methodology and reactions / Synthetic methods
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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