Samarium(II) iodide-mediated intramolecular conjugate additions of alpha,beta-unsaturated lactones

J Org Chem. 2002 May 31;67(11):3861-5. doi: 10.1021/jo0255936.

Abstract

Samarium(II) iodide, in the presence of catalytic amounts of nickel(II) iodide, has been used to promote intramolecular conjugate additions of alkyl halides onto alpha,beta-unsaturated lactones. This process has been shown to be applicable to a number of alpha,beta-unsaturated lactones, including tetrasubstituted olefins, and has been demonstrated to be quite general for the formation of saturated bicyclic and tricyclic lactones. The method presented herein provides a mild, efficient process to form structurally complex lactones from simple precursors.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Cyclization
  • Hydrocarbons, Halogenated / chemistry
  • Iodides / chemistry*
  • Lactones / chemical synthesis*
  • Samarium / chemistry*

Substances

  • Hydrocarbons, Halogenated
  • Iodides
  • Lactones
  • Samarium
  • samarium diiodide