Zinc-mediated chain extension of beta-keto phosphonates.

Academic Article


  • A variety of beta-keto phosphonates can be converted to gamma-keto phosphonates through reaction with ethyl(iodomethyl)zinc. The presence of alpha-alkyl substituents, Lewis basic functionality, and modestly acidic NH-protons are accommodated in substrates of this reaction. Chain extension of beta-keto phosphonates that contained olefinic functionality proceeded more quickly than cyclopropanation; however, it was not possible to effect the chain extension to the exclusion of cyclopropane formation. A primary reason for this imperfect chemoselectivity appears to be the slow chain extension of beta-keto phosphonates. Nevertheless, the simplicity, the scope, and efficiency of this method serve to make it an attractive alternative to the established methods for gamma-keto phosphonate formation.
  • Authors

  • Verbicky, CA
  • Zercher, Charles
  • Status

    Publication Date

  • September 8, 2000
  • Has Subject Area

    Published In

    Digital Object Identifier (doi)

    Pubmed Id

  • 10970300
  • Start Page

  • 5615
  • End Page

  • 5622
  • Volume

  • 65
  • Issue

  • 18