Enamide-benzyne-[2 + 2] cycloaddition: stereoselective tandem [2 + 2]-pericyclic ring-opening-intramolecular N-tethered [4 + 2] cycloadditions

Org Lett. 2009 Aug 20;11(16):3666-9. doi: 10.1021/ol901434g.

Abstract

Benzyne-[2 + 2] cycloadditions with enamides are described. This effort led to the development of a highly stereoselective tandem [2 + 2] cycloaddition-pericyclic ring-opening-intramolecular-N-tethered-[4 + 2] cycloaddition for rapid assembly of nitrogen heterocycles.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Amides / chemistry
  • Benzene Derivatives / chemistry*
  • Combinatorial Chemistry Techniques
  • Cyclization
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Molecular Structure
  • Nitrogen / chemistry*
  • Stereoisomerism

Substances

  • Amides
  • Benzene Derivatives
  • Heterocyclic Compounds
  • benzyne
  • Nitrogen