gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

Michael G. Edwards, Richard J. Paxton, David S. Pugh, Adrian C. Whitwood, Richard J. K. Taylor

Research output: Contribution to journalArticlepeer-review

Abstract

A new nucleophilic isopropyl transfer reagent, triisopropylsulfoxonium tetrafluoroborate, has been prepared and evaluated. Thus, using this reagent and NaH in DMF, a range of electron deficient alkenes, including several chalcone analogues, alpha,beta-unsaturated ketones, dienones and quinones, plus alpha,beta-unsaturated esters, nitrile, sulfone and nitro examples, have been converted into the corresponding gem-dimethylcyclopropane compounds.

Original languageEnglish
Pages (from-to)3279-3288
Number of pages10
JournalSYNTHESIS-STUTTGART
Issue number20
DOIs
Publication statusPublished - 17 Oct 2008

Keywords

  • cyclopropanes
  • cyclopropanation
  • sulfoxonium salts
  • ruthenium tetraoxide
  • TANDEM OXIDATION PROCESSES
  • ALKYLIDENE TRANSFER REAGENTS
  • DIMETHYLSULFOXONIUM METHYLIDE
  • FUNCTIONALIZED CYCLOPROPANES
  • OXOSULFONIUM SALTS
  • DIMETHYL-SULFOXIDE
  • ALLYLIC ALCOHOLS
  • KETONES
  • YLIDES
  • ESTERS

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