Asymmetric hydrogenation of exocyclic γ,δ-unsaturated β-ketoesters to functionalized chiral allylic alcohols <i>via</i> dynamic kinetic resolution
Huai‐Yu Bin, Li Cheng, Wu Xiong, Chang-Liang Zhu, Xiao‐Hui Yang, Jian‐Hua Xie, Qi‐Lin Zhou
Abstract
-selectivities (93 : 7 to >99 : 1). The origin of the excellent stereoselectivity was also rationalized by density functional theory calculations. Furthermore, this protocol could be performed on gram scale and at a lower catalyst loading (0.002 mol%) without the loss of reactivity and enantioselectivity, and has been successfully applied in the enantioselective synthesis of chiral carbocyclic δ-amino esters and the β-galactosidase inhibitor isogalactofagomine.
Topics & Concepts
Kinetic resolutionAllylic rearrangementEnantioselective synthesisIridiumAsymmetric hydrogenationChemistryEnantiomerCatalysisOrganic chemistryCombinatorial chemistryMedicinal chemistryAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisAsymmetric Synthesis and Catalysis