Generation of ortho-quinone methides by p-TsOH on silica and their hetero-Diels-Alder reactions with styrenes

J Org Chem. 2009 May 15;74(10):4009-12. doi: 10.1021/jo900504y.

Abstract

2-Arylchromans were readily prepared from the hetero-Diels-Alder reactions of styrenes with the ortho-quinone methides (o-QMs) which, in turn, were generated by treating the MOM-protected benzylacetate derivatives with p-TsOH immobilized on silica (PTS-Si) in toluene under mild conditions (0 degrees C to rt). The corresponding chromans were obtained in moderate to excellent yields (42-97%) and in moderate to excellent diastereoselectivity (up to >99:1).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromans / chemical synthesis
  • Chromans / chemistry
  • Indolequinones / chemical synthesis*
  • Indolequinones / chemistry
  • Silicon Dioxide / chemistry*
  • Styrene / chemistry*
  • Toluene / analogs & derivatives*
  • Toluene / chemistry

Substances

  • Chromans
  • Indolequinones
  • quinone methide
  • Toluene
  • Styrene
  • Silicon Dioxide
  • 4-toluenesulfinic acid