Enantioselective Synthesis of Pyrazolo[3,4-b]pyridone Derivatives with Antifungal Activities against Phytophthora capsici and Colletotrichum fructicola.

A chiral NHC-catalyzed [3 + 3] cycloaddition reaction is developed for the efficient synthesis of pyrazolo[3,4-b]pyridones in generally excellent yields and optical purities. The R, S, and racemic forms of these molecules are systematically studied via in vitro tests that detect antifungal activity against Phytophthora capsici and Colletotrichum fructicola. Chiral compounds (R)-3i, (R)-3j, and (R)-3p are identified to have excellent inhibitory effects against P. capsici and C. fructicola.