An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate

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

Research output: Contribution to journalArticlepeer-review

Abstract

A new procedure for the cyclopropanation of alpha,beta-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of alpha,beta-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropoyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.

Original languageEnglish
Pages (from-to)521-524
Number of pages4
JournalSynlett
Issue number4
DOIs
Publication statusPublished - 3 Mar 2008

Keywords

  • cyclopropanes
  • cyclopropanation
  • tandem oxidation procedures
  • sulfoxonium salts
  • ruthenium tetroxide
  • TANDEM OXIDATION PROCESSES
  • ALKYLIDENE TRANSFER REAGENTS
  • ORGANIC-SYNTHESIS
  • DIMETHYLSULFOXONIUM METHYLIDE
  • FUNCTIONALIZED CYCLOPROPANES
  • OXOSULFONIUM SALTS
  • ALLYLIC ALCOHOLS
  • ESTERS
  • YLIDES

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