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gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

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

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.

    Research areas

  • 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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