Get access

Recognition and Site-Selective Transformation of Monosaccharides by Using Copper(II) Catalysis

Authors

  • Dr. I-Hon Chen,

    1. Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA)
    Search for more papers by this author
  • Kevin G. M. Kou,

    1. Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA)
    2. Department of Chemistry, University of Toronto, 80 St. George Street (Canada)
    Search for more papers by this author
  • Diane N. Le,

    1. Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA)
    Search for more papers by this author
  • Colin M. Rathbun,

    1. Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA)
    Search for more papers by this author
  • Prof. Dr. Vy M. Dong

    Corresponding author
    1. Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA)
    • Department of Chemistry, University of California, Irvine, Natural Sciences 1, University of California, Irvine, California 92697 (USA)

    Search for more papers by this author

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.

Get access to the full text of this article

Ancillary