Regio- and stereoselective synthesis of 2-deoxy-C-aryl glycosides via palladium catalyzed decarboxylative reactions

Org Lett. 2011 Sep 2;13(17):4608-11. doi: 10.1021/ol201820m. Epub 2011 Aug 4.

Abstract

An efficient and versatile approach for the synthesis of 2-deoxy-C-aryl glycosides is reported. This strategy is based on a palladium-catalyzed decarboxylative Heck coupling reaction of benzoic acids and glycals. A wide variety of glycals and benzoic acids have been screened, and all these reactions could afford the desired C-aryl glycoside products in moderate to good yields with exclusive regio- and stereoselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Crystallography, X-Ray
  • Decarboxylation
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Models, Molecular
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Glycosides
  • Organometallic Compounds
  • Palladium