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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Bibliographic Details
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
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REAGENT
NITRO-GROUP
POTENT
ELECTRONICALLY EFFECTIVE CARBONYL
TRIFLUOROMETHANESULFONYL AZIDE
OLEFINS
PRINCIPLE
ANTIINFLAMMATORY 4,5-DIARYLPYRROLES
DERIVATIVES
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol050442l