Palladium/Xiao‐Phos‐Catalyzed Kinetic Resolution of <i>sec</i>‐Phosphine Oxides by <i>P</i>‐Benzylation
Qiang Dai, Lu Liu, Junliang Zhang
Abstract
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
Kinetic resolutionPhosphinePalladiumStereocenterCatalysisChemistryDenticityEnantioselective synthesisYield (engineering)PhosSelectivityCombinatorial chemistryOrganic chemistryMetalMedicinal chemistryStereochemistryMaterials scienceBiochemistryMetallurgyAsymmetric Hydrogenation and CatalysisAsymmetric Synthesis and CatalysisSynthetic Organic Chemistry Methods