Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents
Qianwen He, Dong Zhang, Fengcai Zhang, Xiaohua Liu, Xiaoming Feng
Abstract
An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.
Topics & Concepts
ChemistryAntifungalCatalysisCombinatorial chemistryTerminal (telecommunication)TriazoleStereochemistryOrganic chemistryMicrobiologyComputer scienceTelecommunicationsBiologyClick Chemistry and ApplicationsChemical Synthesis and ReactionsSynthesis and Catalytic Reactions