Intermolecular Ene Reactions Utilizing Oxazolones and Enol Ethers

We report herein an intermolecular ene reaction using oxazolones with enol ethers which results in the formation of novel quaternary amino esters in near quantitative yields. The overall reaction transformation closely resembles an intermolecular version of the Conia-ene reaction. The reactions are...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 129; no. 11; pp. 3058 - 3059
Main Authors Fisk, Jason S, Tepe, Jetze J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.03.2007
Amer Chemical Soc
Subjects
Alkenes - chemistry
Chemistry
Chemistry, Multidisciplinary
Cyclization
Esters - chemistry
Ethers - chemistry
Ketones - chemical synthesis
Oxazolone - analogs & derivatives
Oxazolone - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
AZLACTONES
CATALYZED CYCLOISOMERIZATION
TRIACETATES
BETA-KETOESTERS
CONSTRUCTION
CARBOCYCLIZATION
ARYLATION
CARBONYL-COMPOUNDS
ALKYNES
CYCLIZATION
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Summary:We report herein an intermolecular ene reaction using oxazolones with enol ethers which results in the formation of novel quaternary amino esters in near quantitative yields. The overall reaction transformation closely resembles an intermolecular version of the Conia-ene reaction. The reactions are uncatalyzed and occur under very mild conditions.
Bibliography:istex:244A39EBE861B4ABFDCAF79DC88172FDC35B4932
ark:/67375/TPS-TMRNP5PF-5
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0002-7863
1520-5126
DOI:10.1021/ja0627904