SEARCH

SEARCH BY CITATION

Keywords:

  • carbohydrates;
  • catalysis;
  • molecular recognition;
  • site-selective functionalization;
  • transition metals

Abstract

We demonstrate copper(II)-catalyzed acylation and tosylation of monosaccharides. Various carbohydrate derivatives, including glucopyranosides and ribofuranosides, are obtained in high yields and regioselectivities. Using this versatile strategy, the site of acylation can be switched by choice of ligand. Preliminary mechanistic studies support nucleophilic addition of a copper–sugar complex to the acyl chloride to be turnover limiting.