Four-component domino reaction providing an easy access to multifunctionalized tricyclo[6.2.2.0(1,6)]dodecane derivatives

J Org Chem. 2010 May 7;75(9):2962-5. doi: 10.1021/jo1002278.

Abstract

A novel four-component domino reaction has been discovered. The reaction is easy to perform simply by mixing four common reactants and Cs(2)CO(3) in ethylene glycol under microwave heating. The reaction proceeds at fast rates and can be finished within 15-24 min, which makes workup convenient. Four stereogenic centers with one quaternary carbon-amino function have been controlled completely. The stereochemistry has been unequivocally determined by X-ray structural analysis. The resulting tricyclo[6.2.2.0(1,6)]dodecane derivatives are of importance for organic and medicinal research.

Publication types

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

MeSH terms

  • Alkanes / chemical synthesis*
  • Carbonates / chemistry*
  • Cesium / chemistry*
  • Ethylene Glycol / chemistry*
  • Microwaves
  • Molecular Structure
  • Polycyclic Compounds / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkanes
  • Carbonates
  • Polycyclic Compounds
  • n-dodecane
  • Cesium
  • Ethylene Glycol
  • cesium carbonate