Facile synthesis of enantiomerically pure 2- and 2,3-disubstituted furans catalysed by mixed Lewis acids: an easy route to 3-iodofurans and 3-(hydroxymethyl)furans

Chemistry. 2009 Jun 8;15(24):6041-9. doi: 10.1002/chem.200900007.

Abstract

Simple and efficient syntheses, catalysed by a mixed Lewis acid system (ZrCl(4)/ZnI(2)), of enantiomerically pure 2- and 2,3-disubstituted furan derivatives--including important synthons such as 3-iodofuran and 3-(hydroxymethyl)furan derivatives--from commercially available 3,4,6-tri-O-acetyl-D-glucal are described. The transformation is achieved through a synergistic interaction between ZrCl(4) and ZnI(2) in catalytic amounts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chlorides / chemistry
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Iodides / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism
  • Zinc Compounds / chemistry

Substances

  • Chlorides
  • Furans
  • Iodides
  • Zinc Compounds
  • zinc iodide
  • zinc chloride