Doubly Activated Cyclopropanes as Synthetic Precursors for the Preparation of 4-Nitro- and 4-Cyano-dihydropyrroles and Pyrroles

1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in situ-generated phenyliodonium ylides catalyzed by Rh(II) carboxylates. The doubly activated cyclopropanes were used as synthetic precursors for the r...

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Published inOrganic letters Vol. 7; no. 12; pp. 2313 - 2316
Main Authors Wurz, Ryan P, Charette, André B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 09.06.2005
Amer Chemical Soc
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Abstract 1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in situ-generated phenyliodonium ylides catalyzed by Rh(II) carboxylates. The doubly activated cyclopropanes were used as synthetic precursors for the regiospecific synthesis of 4-nitro- and 4-cyano-dihydropyrroles upon treatment with primary amines. Oxidation of the dihydropyrroles with DDQ allows rapid access to densely functionalized pyrroles.
AbstractList [reaction: see text] 1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in situ-generated phenyliodonium ylides catalyzed by Rh(II) carboxylates. The doubly activated cyclopropanes were used as synthetic precursors for the regiospecific synthesis of 4-nitro- and 4-cyano-dihydropyrroles upon treatment with primary amines. Oxidation of the dihydropyrroles with DDQ allows rapid access to densely functionalized pyrroles.
1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in situ-generated phenyliodonium ylides catalyzed by Rh(II) carboxylates. The doubly activated cyclopropanes were used as synthetic precursors for the regiospecific synthesis of 4-nitro- and 4-cyano-dihydropyrroles upon treatment with primary amines. Oxidation of the dihydropyrroles with DDQ allows rapid access to densely functionalized pyrroles.
Author Charette, André B
Wurz, Ryan P
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  givenname: André B
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/15932186$$D View this record in MEDLINE/PubMed
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Issue 12
Keywords REAGENT
NITRO-GROUP
POTENT
ELECTRONICALLY EFFECTIVE CARBONYL
TRIFLUOROMETHANESULFONYL AZIDE
OLEFINS
PRINCIPLE
ANTIINFLAMMATORY 4,5-DIARYLPYRROLES
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Snippet 1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo compounds or in...
[reaction: see text] 1-Nitro- and 1-cyano-cyclopropyl ketones have been prepared in an expedient manner from cyclopropanation reactions of alkenes by diazo...
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SubjectTerms Chemistry
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Physical Sciences
Science & Technology
Title Doubly Activated Cyclopropanes as Synthetic Precursors for the Preparation of 4-Nitro- and 4-Cyano-dihydropyrroles and Pyrroles
URI http://dx.doi.org/10.1021/ol050442l
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