Dynamic Kinetic Resolution of γ-Substituted Cyclic β-Ketoesters via Asymmetric Hydrogenation: Constructing Chiral Cyclic β-Hydroxyesters with Three Contiguous Stereocenters
Dan Yang, Wu Xiong, Xiaojie Zheng, Jian‐Hua Xie, Qi‐Lin Zhou
Abstract
An efficient asymmetric hydrogenation of racemic γ-substituted cyclic β-ketoesters via dynamic kinetic resolution to provide chiral cyclic β-hydroxy esters with three contiguous stereocenters is reported. Using a chiral spiro iridium catalyst (R)-5 (Ir-SpiroSAP), a series of racemic γ-aryl/alkyl substituted cyclic β-ketoesters were hydrogenated to the corresponding chiral cyclic β-hydroxy esters in high yields (84–97%) with good to excellent enantioselectivities (69–>99% ee) and cis,cis-selectivities (up to >99:1).
Topics & Concepts
StereocenterChemistryKinetic resolutionCatalysisAsymmetric hydrogenationAlkylArylEnantioselective synthesisStereochemistryResolution (logic)Medicinal chemistryOrganic chemistryComputer scienceArtificial intelligenceAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisAsymmetric Synthesis and Catalysis