Access to chiral phthalidyl ester prodrugs <i>via</i> an isothiourea-catalyzed dynamic kinetic resolution reaction

An isothiourea-catalyzed acylative dynamic kinetic resolution reaction has been developed for the synthesis of chiral phthalidyl ester prodrugs. Various chiral phthalidyl esters were obtained in moderate to excellent yields (up to 97%) and good to excellent optical purities (up to 99 : 1 er). Notably, a variety of acyl chlorides were well tolerated, even those derived from pharmaceuticals, agrochemicals, and natural products. This catalytic transformation is an effective strategy for the development of chiral phthalidyl ester prodrugs.