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gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

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gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations. / Edwards, Michael G.; Paxton, Richard J.; Pugh, David S.; Whitwood, Adrian C.; Taylor, Richard J. K.

In: SYNTHESIS-STUTTGART, No. 20, 17.10.2008, p. 3279-3288.

Research output: Contribution to journalArticlepeer-review

Harvard

Edwards, MG, Paxton, RJ, Pugh, DS, Whitwood, AC & Taylor, RJK 2008, 'gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations', SYNTHESIS-STUTTGART, no. 20, pp. 3279-3288. https://doi.org/10.1055/s-0028-1083165

APA

Edwards, M. G., Paxton, R. J., Pugh, D. S., Whitwood, A. C., & Taylor, R. J. K. (2008). gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations. SYNTHESIS-STUTTGART, (20), 3279-3288. https://doi.org/10.1055/s-0028-1083165

Vancouver

Edwards MG, Paxton RJ, Pugh DS, Whitwood AC, Taylor RJK. gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations. SYNTHESIS-STUTTGART. 2008 Oct 17;(20):3279-3288. https://doi.org/10.1055/s-0028-1083165

Author

Edwards, Michael G. ; Paxton, Richard J. ; Pugh, David S. ; Whitwood, Adrian C. ; Taylor, Richard J. K. / gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations. In: SYNTHESIS-STUTTGART. 2008 ; No. 20. pp. 3279-3288.

Bibtex - Download

@article{5de9baf0d669415783329bb46bf8b7e2,
title = "gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations",
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.",
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",
author = "Edwards, {Michael G.} and Paxton, {Richard J.} and Pugh, {David S.} and Whitwood, {Adrian C.} and Taylor, {Richard J. K.}",
year = "2008",
month = oct,
day = "17",
doi = "10.1055/s-0028-1083165",
language = "English",
pages = "3279--3288",
journal = "SYNTHESIS-STUTTGART",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "20",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

AU - Edwards, Michael G.

AU - Paxton, Richard J.

AU - Pugh, David S.

AU - Whitwood, Adrian C.

AU - Taylor, Richard J. K.

PY - 2008/10/17

Y1 - 2008/10/17

N2 - 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.

AB - 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.

KW - cyclopropanes

KW - cyclopropanation

KW - sulfoxonium salts

KW - ruthenium tetraoxide

KW - TANDEM OXIDATION PROCESSES

KW - ALKYLIDENE TRANSFER REAGENTS

KW - DIMETHYLSULFOXONIUM METHYLIDE

KW - FUNCTIONALIZED CYCLOPROPANES

KW - OXOSULFONIUM SALTS

KW - DIMETHYL-SULFOXIDE

KW - ALLYLIC ALCOHOLS

KW - KETONES

KW - YLIDES

KW - ESTERS

UR - http://www.scopus.com/inward/record.url?scp=55349131712&partnerID=8YFLogxK

U2 - 10.1055/s-0028-1083165

DO - 10.1055/s-0028-1083165

M3 - Article

SP - 3279

EP - 3288

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

SN - 0039-7881

IS - 20

ER -