Acylative and Silylative Dynamic Kinetic Resolutions of 6-Hydroxy-2H-pyran-3(6H)-one Catalyzed by Chiral Guanidines

Abstract

AbstractChiral guanidine-catalyzed acylative and silylative dynamic kinetic resolutions of 6-hydroxy-2H-pyran-3(6H)-one were achieved. We succeeded in developing a non-enzymatic acylative dynamic kinetic resolution of 6-hydroxy-2H-pyran-3(6H)-one with high enantioselectivity, which could be improved by recrystallization. In contrast, the non-enzymatic silylative dynamic kinetic resolution of 6-hydroxy-2H-pyran-3(6H)-one was accomplished with a moderate selectivity for the first time.