gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

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

doi:10.1055/s-0028-1083165

gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

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

Chemistry

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

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.

Original language	English
Pages (from-to)	3279-3288
Number of pages	10
Journal	SYNTHESIS-STUTTGART
Issue number	20
DOIs	https://doi.org/10.1055/s-0028-1083165
Publication status	Published - 17 Oct 2008

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

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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.",

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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,

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doi = "10.1055/s-0028-1083165",

language = "English",

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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

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U2 - 10.1055/s-0028-1083165

DO - 10.1055/s-0028-1083165

M3 - Article

SN - 0039-7881

SP - 3279

EP - 3288

JO - SYNTHESIS-STUTTGART

JF - SYNTHESIS-STUTTGART

IS - 20

ER -

gem-Dimethylcyclopropanation Using Triisopropylsulfoxonium Tetrafluoroborate: Scope and Limitations

Abstract

Keywords

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