Anion-Bridged Dual Hydrogen Bond Enabled Concerted Addition of Phenol to Glycal.

ABSTRACT: A noncovalent organocatalytic concerted addition of phenol to glycal is developed for the stereoselective and regioselective construction of biologically important phenolic 2-deoxyglycosides, featuring wide substrate tolerance. The method relies on an anion-bridged dual hydrogen bond interaction which is experimentally proved by Nuclear Magnetic Resonance (NMR), Ultraviolet and visible (UV-vis), and fluorescence analysis. Experimental evidence including kinetic analysis, Kinetic Isotope Effect (KIE) studies, linear free energy relationship, Hammett plot, and density functional theory (DFT) calculations is provided for a concerted mechanism where a high-energy oxocarbenium ion is not formed. In addition, the potential utility of this method is further demonstrated by the synthesis of biolog

SUBMITTER: Jiao Q 

PROVIDER: S-EPMC10953558 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature