Oxidant-controlled heck-type C-glycosylation of glycals with arylboronic acids: stereoselective synthesis of aryl 2-deoxy-C-glycosides

Org Lett. 2009 Apr 16;11(8):1709-12. doi: 10.1021/ol900273d.

Abstract

Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)(2) as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained with benzoquinone (BQ), Cu(OAc)(2)/O(2), and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidants, respectively. This method provides a simple, mild, and stereoselective synthesis of aryl 2-deoxy-C-glycosides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoquinones / chemistry*
  • Boronic Acids / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ethers, Cyclic / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosylation
  • Molecular Structure
  • Oxidants / chemistry
  • Stereoisomerism

Substances

  • Benzoquinones
  • Boronic Acids
  • Ethers, Cyclic
  • Glycosides
  • Oxidants
  • dichlorodicyanobenzoquinone