Synthesis of Lactams via Copper-Catalyzed Intramolecular Vinylation of Amides

Copper-catalyzed intramolecular vinylation of iodoenamides were investigated for the first time. With CuI as the catalyst and N,N ‘-dimethylethylenediamine as the ligand, a number of iodoenamides underwent cyclization in dioxane leading to the formations of five- to seven-membered lactams in moderat...

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Published inOrganic letters Vol. 7; no. 10; pp. 2035 - 2038
Main Authors Hu, Tianshun, Li, Chaozhong
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 12.05.2005
Amer Chemical Soc
Subjects
Amides - chemistry
Catalysis
Chemistry
Chemistry, Organic
Copper - chemistry
Cyclization
Lactams - chemical synthesis
Molecular Structure
Physical Sciences
Science & Technology
AMINATION
ETHERS
GOLDBERG REACTIONS
ONE-POT SYNTHESIS
ARYL HALIDES
AMIDATION
N-ARYLATION
ULLMANN
STEREOCONTROLLED SYNTHESIS
ENAMIDES
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Summary:Copper-catalyzed intramolecular vinylation of iodoenamides were investigated for the first time. With CuI as the catalyst and N,N ‘-dimethylethylenediamine as the ligand, a number of iodoenamides underwent cyclization in dioxane leading to the formations of five- to seven-membered lactams in moderate to excellent yields.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol0505555