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gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

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

*Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK, Email:

M. G. Edwards, R. J. Paxton, D. S. Pugh, A. C. Whitwood, R. J. K. Taylor, Synthesis, 2008, 3279-3288.

DOI: 10.1055/s-0028-1083165


A new nucleophilic isopropyl transfer reagent, triisopropylsulfoxonium tetrafluoroborate, converts after deprotonation with NaH a range of electron deficient alkenes, including several chalcone analogues, α,β-unsaturated ketones, dienones and quinones, plus α,β-unsaturated esters, nitrile, sulfone and nitro examples into the corresponding gem-dimethylcyclopropane compounds.

see article for more examples

Improved Dimethylsulfoxonium Methylide Cyclopropanation Procedures, Including a Tandem Oxidation Variant

R. J. Paxton, R. J. K. Taylor, Synlett, 2007, 633-637.

Key Words

cyclopropanes, cyclopropanation, sulfoxonium salts, ruthenium tetraoxide, Corey-Chaykowsky Reaction

ID: J66-Y2008-3040