Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction

J Am Chem Soc. 2008 Apr 2;130(13):4517-26. doi: 10.1021/ja711058f. Epub 2008 Mar 8.

Abstract

Tris(triphenylphosphinegold) oxonium tetrafluoroborate, [(Ph3PAu)3O]BF4, catalyzes the rearrangement of 1,5-allenynes to produce cross-conjugated trienes. Experimental and computational evidence shows that the ene reaction proceeds through a unique nucleophilic addition of an allene double bond to a cationic phosphinegold(I)-complexed phosphinegold(I) acetylide, followed by a 1,5-hydrogen shift.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkadienes / chemical synthesis*
  • Alkadienes / chemistry
  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Models, Chemical
  • Molecular Structure
  • Organogold Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alkadienes
  • Alkynes
  • Organogold Compounds