Palladium/Xiao‐Phos‐Catalyzed Kinetic Resolution of <i>sec</i>‐Phosphine Oxides by <i>P</i>‐Benzylation
Qiang Dai, Lu Liu, Junliang Zhang
Abstract
P-stereogenic tert- and sec-phosphines have wide applications in asymmetric catalysis, materials, and pharmaceutical chemistry, however, their practical synthesis still constitutes a significant challenge. Herein, a successful kinetic resolution of rac-secondary phosphine oxides via the enantioselective P-benzylation process catalyzed by the palladium/Xiao-Phos was designed. Both tert- and sec-phosphine oxides were delivered in good yield and excellent enantiopurity (selectivity factor up to 226.1). The appealing synthetic utilities are further demonstrated by the facile preparation of several valuable P-chiral compounds, precursors of bidentate ligands, as well as transition metal complexes.
Topics & Concepts
PhosphineKinetic resolutionPalladiumStereocenterCatalysisChemistryDenticityPhosYield (engineering)Enantioselective synthesisSelectivityCombinatorial chemistryTransition metalOrganic chemistryMetalMedicinal chemistryStereochemistryMaterials scienceMetallurgyBiochemistryAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods