Novel Axially Chiral Ligand-Enabled Copper-Catalyzed Asymmetric Oxidative Coupling of 2-Naphthols for the Synthesis of 6,6′-Disubstituted BINOLs
Pengyang Wang, Shouyi Cen, Jun Gao, Ahui Shen, Zhipeng Zhang
Abstract
Novel axially chiral ligands have been designed and synthesized by merging the chelating picolinic acid with substituted BINOLs. The in-situ-prepared copper catalysts from the ligands and CuI enable the asymmetric oxidative coupling of 2-naphthols, affording 6,6'-disubstituted BINOLs in up to 89% yield with good enantioselectivities (up to 96:4 e.r.).
Topics & Concepts
ChemistryPicolinic acidCatalysisYield (engineering)CopperLigand (biochemistry)Oxidative coupling of methaneCombinatorial chemistryAxial symmetryChelationOxidative phosphorylationCoupling (piping)Axial chiralityChiral ligandEnantioselective synthesisOrganic chemistryReceptorBiochemistryMechanical engineeringMetallurgyStructural engineeringMaterials scienceEngineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAlkaloids: synthesis and pharmacology