Stereocontrolled formation of ketomethylene isosteres through tandem chain extension reactions.

Academic Article


  • A zinc-mediated chain extension reaction is the key step in the preparation of gamma-keto amides derived from amino acids. The use of tandem reaction sequences, in which the intermediate zinc enolate is trapped with electrophilic reagents, results in the incorporation of alpha-substituents, which mimic the side chains found in natural amino acid systems. Use of the chiral amino acid L-proline as a stereo-directing element provides a diastereoselective route to various ketomethylene isosteres.
  • Authors

  • Lin, Weimin
  • Tryder, Nancy
  • Su, Fan
  • Zercher, Charles
  • Jasinski, Jerry P
  • Butcher, Ray J
  • Status

    Publication Date

  • October 13, 2006
  • Has Subject Area

    Published In


  • Ketones
  • Digital Object Identifier (doi)

    Pubmed Id

  • 17025303
  • Start Page

  • 8140
  • End Page

  • 8145
  • Volume

  • 71
  • Issue

  • 21