An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate

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

doi:10.1055/s-2008-1042761

An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate

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

Chemistry

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

Abstract

A new procedure for the cyclopropanation of alpha,beta-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of alpha,beta-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropoyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.

Original language	English
Pages (from-to)	521-524
Number of pages	4
Journal	Synlett
Issue number	4
DOIs	https://doi.org/10.1055/s-2008-1042761
Publication status	Published - 3 Mar 2008

Keywords

cyclopropanes
cyclopropanation
tandem oxidation procedures
sulfoxonium salts
ruthenium tetroxide
TANDEM OXIDATION PROCESSES
ALKYLIDENE TRANSFER REAGENTS
ORGANIC-SYNTHESIS
DIMETHYLSULFOXONIUM METHYLIDE
FUNCTIONALIZED CYCLOPROPANES
OXOSULFONIUM SALTS
ALLYLIC ALCOHOLS
ESTERS
YLIDES

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title = "An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate",

abstract = "A new procedure for the cyclopropanation of alpha,beta-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of alpha,beta-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropoyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.",

keywords = "cyclopropanes, cyclopropanation, tandem oxidation procedures, sulfoxonium salts, ruthenium tetroxide, TANDEM OXIDATION PROCESSES, ALKYLIDENE TRANSFER REAGENTS, ORGANIC-SYNTHESIS, DIMETHYLSULFOXONIUM METHYLIDE, FUNCTIONALIZED CYCLOPROPANES, OXOSULFONIUM SALTS, ALLYLIC ALCOHOLS, ESTERS, YLIDES",

author = "Edwards, {Michael G.} and Paxton, {Richard J.} and Pugh, {David S.} and Taylor, {Richard J. K.}",

year = "2008",

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doi = "10.1055/s-2008-1042761",

language = "English",

pages = "521--524",

journal = "Synlett",

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T1 - An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate

AU - Edwards, Michael G.

AU - Paxton, Richard J.

AU - Pugh, David S.

AU - Taylor, Richard J. K.

PY - 2008/3/3

Y1 - 2008/3/3

N2 - A new procedure for the cyclopropanation of alpha,beta-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of alpha,beta-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropoyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.

AB - A new procedure for the cyclopropanation of alpha,beta-unsaturated carbonyl compounds and related systems is described which employs triisopropylsulfoxonium tetrafluoroborate and sodium hydride in dimethylformamide. Using this reagent, a range of alpha,beta-unsaturated ketones (and an ester and a vinyl nitro example) has been converted into the corresponding gem-dimethylcyclopropoyl carbonyl compounds; in addition, a preliminary result is described in which an activated alcohol is converted directly into a gem-dimethylyclopropyl ketone by a one-pot tandem oxidation-cyclopropanation sequence, albeit in low yield.

KW - cyclopropanes

KW - cyclopropanation

KW - tandem oxidation procedures

KW - sulfoxonium salts

KW - ruthenium tetroxide

KW - TANDEM OXIDATION PROCESSES

KW - ALKYLIDENE TRANSFER REAGENTS

KW - ORGANIC-SYNTHESIS

KW - DIMETHYLSULFOXONIUM METHYLIDE

KW - FUNCTIONALIZED CYCLOPROPANES

KW - OXOSULFONIUM SALTS

KW - ALLYLIC ALCOHOLS

KW - ESTERS

KW - YLIDES

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U2 - 10.1055/s-2008-1042761

DO - 10.1055/s-2008-1042761

M3 - Article

SP - 521

EP - 524

JO - Synlett

JF - Synlett

SN - 1437-2096

IS - 4

ER -

An improved gem-dimethylcyclopropanation procedure using triisopropylsulfoxonium tetrafluoroborate

Abstract

Keywords

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