Ligand-Enabled, Copper-Catalyzed Electrophilic Amination for the Asymmetric Synthesis of β-Amino Acids
Raj Kumar Tak, Hidetoshi Noda, Masakatsu Shibasaki
Abstract
Catalytic asymmetric nitrene transfer has emerged as a reliable method for the synthesis of nitrogen-containing chiral compounds. Herein, we report the copper-catalyzed intramolecular asymmetric electrophilic amination of aromatic rings. The reactive intermediate is a copper-alkyl nitrene generated from isoxazolidin-5-ones. Copper catalysis promotes three classes of asymmetric transformations, namely, asymmetric desymmetrization, parallel kinetic resolution, and kinetic resolution, expanding the repertoire of alkyl nitrene transfer and providing various cyclic and linear β-amino acids in their enantioenriched forms.
Topics & Concepts
NitreneChemistryAminationKinetic resolutionElectrophilic aminationDesymmetrizationElectrophileCombinatorial chemistryCatalysisIntramolecular forceAlkylLigand (biochemistry)Enantioselective synthesisCopperHydroaminationOrganic chemistryStereochemistryReceptorBiochemistrySynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and Catalysis