gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

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Research output: Contribution to journal › Article › peer-review

Published copy (DOI)

10.1055/s-0028-1083165

Author(s)

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

Department/unit(s)

Chemistry

Publication details

Journal	SYNTHESIS-STUTTGART
Date	Published - 17 Oct 2008
Issue number	20
Number of pages	10
Pages (from-to)	3279-3288
Original language	English

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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