Au-containing all-carbon 1,3-dipoles: generation and [3+2] cycloaddition reactions

J Am Chem Soc. 2008 Sep 24;130(38):12598-9. doi: 10.1021/ja804690u. Epub 2008 Aug 28.

Abstract

A novel approach to generate Au-containing all-carbon 1,3-dipoles is developed via an unprecedented migration-fragmentation of ketals/acetals. These in situ generated dipoles undergo rapid [3+2] cycloaddition under mild conditions with various enones/enals, electron-rich aromatic aldehydes, and N-benzylindole, leading to flexible formation of highly functionalized dihydrofurans and cyclopentenes.

Publication types

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

MeSH terms

  • Acetals / chemistry
  • Alkenes / chemical synthesis
  • Alkenes / chemistry*
  • Alkynes / chemistry*
  • Benzaldehydes / chemistry
  • Cyclization
  • Furans / chemical synthesis*
  • Gold / chemistry*
  • Ketones / chemistry*
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / chemistry

Substances

  • Acetals
  • Alkenes
  • Alkynes
  • Benzaldehydes
  • Furans
  • Ketones
  • Organometallic Compounds
  • Gold
  • 4-anisaldehyde