Copper-Catalyzed Vinylation of Hydrazides. A Regioselective Entry to Highly Substituted Pyrroles

A modular route to highly substituted pyrroles has been developed. This transformation consists of two sequential copper-catalyzed vinylations of bis-Boc-hydrazine followed by thermal rearrangement/cyclization. A wide variety of functionalized pyrroles can be prepared in a selective manner from simp...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 6; pp. 973 - 976
Main Authors Rivero, Marta Rodríguez, Buchwald, Stephen L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2007
Amer Chemical Soc
Subjects
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Cyclization
Hydrazines - chemical synthesis
Models, Chemical
Physical Sciences
Pyrroles - chemistry
Science & Technology
Stereoisomerism
Vinyl Compounds - chemistry
KETONES
GENERAL-SYNTHESIS
ACIDS
EFFICIENT SYNTHESIS
DERIVATIVES
ULLMANN
CYCLIZATION
INDOLES
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Summary:A modular route to highly substituted pyrroles has been developed. This transformation consists of two sequential copper-catalyzed vinylations of bis-Boc-hydrazine followed by thermal rearrangement/cyclization. A wide variety of functionalized pyrroles can be prepared in a selective manner from simple and easily accessible precursors.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol062978s