Iron(III)-catalyzed Conia-ene cyclization of 2-alkynic 1,3-dicarbonyl compounds

J Org Chem. 2012 Jun 15;77(12):5239-44. doi: 10.1021/jo300957q. Epub 2012 May 30.

Abstract

A cheap, simple, and effective FeCl(3)-catalyzed Conia-ene cyclization of 2-alkynic 1,3-dicarbonyl compounds was stereospecific to afford alkylidenecyclopentanes in (E)-isomers via the 5-exo-dig pathway. The 5-endo-dig and 6-exo-dig cyclizations were also possible, depending on the structure of the substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Cyclization
  • Cyclopentanes / chemistry*
  • Ferric Compounds / chemistry*
  • Iron / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkynes
  • Chlorides
  • Cyclopentanes
  • Ferric Compounds
  • Iron
  • ferric chloride