Palladium-catalyzed intramolecular cyanoamidation of alkynyl and alkenyl cyanoformamides

Org Lett. 2006 Jun 22;8(13):2711-3. doi: 10.1021/ol060733+.

Abstract

[reaction: see text] The five- to seven-membered alpha-alkylidene lactams were prepared in 45-99% yield by the palladium-catalyzed cyanoamidation of alkynyl cyanoformamides. The reaction proceeded exclusively in a 5-exo mode, giving the corresponding (Z)-alkenes as major products. The reaction was also applied to 1,1-disubstituted alkenes to afford oxindoles bearing a quaternary carbon center.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Amides / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Lactams / chemical synthesis*
  • Molecular Structure
  • Nitriles / chemistry*
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Alkynes
  • Amides
  • Lactams
  • Nitriles
  • Palladium