Iridium-Catalyzed Asymmetric Hydrogenation of α-Fluoro Ketones via a Dynamic Kinetic Resolution Strategy
Xuefeng Tan, Weijun Zeng, Jialin Wen, Xumu Zhang
Abstract
The discrimination of a fluorine atom from a hydrogen atom has been challenging in asymmetric catalysis. We herein report iridium-catalyzed hydrogenation of α-fluoro ketones using a strategy of dynamic kinetic resolution. Both enantiomeric and diastereomeric selectivities were satisfactory in the preparation of β-fluoro alcohols. The DFT calculation revealed a C-F···Na charge-dipole interaction in the transition state of hydride transfer. This noncovalent interaction would be responsible for the diastereomeric control.
Topics & Concepts
ChemistryDiastereomerIridiumCatalysisKinetic resolutionEnantiomerHydrideFluorineEnantioselective synthesisHydrogen atomAsymmetric hydrogenationComputational chemistryHydrogenCombinatorial chemistryOrganic chemistryAlkylAsymmetric Hydrogenation and CatalysisCarbon dioxide utilization in catalysisFluorine in Organic Chemistry