Iron-catalyzed rearrangements and cycloaddition reactions of 2H-chromenes

Org Lett. 2011 Dec 16;13(24):6480-3. doi: 10.1021/ol202772k. Epub 2011 Nov 18.

Abstract

Iron(III) salts catalyze the tandem rearrangement/hetero-Diels-Alder reaction of 2H-chromenes to yield tetrahydrochromeno heterocycles. The process can occur as a homodimerization and cycloaddition process using electron-rich dienophiles. Deuterium labeling and mechanistic studies revealed a hydride shift and ortho-quinone methide cycloaddition reaction pathway.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Ferric Compounds / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Indolequinones / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Benzopyrans
  • Ferric Compounds
  • Heterocyclic Compounds
  • Indolequinones
  • quinone methide