Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition

Org Lett. 2010 Mar 19;12(6):1152-5. doi: 10.1021/ol902821w.

Abstract

A new torquoselective ring-closure of chiral amide-substituted 1,3,5-hexatrienes and its application in tandem with [4 + 2] cycloaddition are described. The trienes were derived via either a 1,3-H or 1,3-H-1,7-H shift of alpha-substituted allenamides, and the entire sequence through the [4 + 2] cycloaddition could be in tandem from allenamides.

Publication types

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

MeSH terms

  • Amides / chemistry*
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Conformation
  • Polyenes / chemical synthesis*
  • Polyenes / chemistry
  • Stereoisomerism

Substances

  • Amides
  • Polyenes
  • 1,3,5-hexatriene