Multisubstituted furan formation from (Z)- or (E)-enynyl acetates: tandem reactions accelerated by electron-donating groups on aromatic rings

J Org Chem. 2012 Apr 20;77(8):3944-51. doi: 10.1021/jo300251c. Epub 2012 Mar 29.

Abstract

Multisubstituted furans were readily prepared from (Z)- or (E)-conjugated enynyl acetates with NXS under metal-free conditions at room temperature via the same haloallenyl ketone intermediates. This tandem haloallenyl ketone formation-furan formation reaction sequence was accelerated by electron-donating groups on the aromatic rings.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Alkadienes / chemistry*
  • Electrons
  • Furans / chemistry*
  • Ketones / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Acetates
  • Alkadienes
  • Furans
  • Ketones
  • furan