An Intramolecular [2 + 2] Cycloaddition of Ketenimines via Palladium-Catalyzed Rearrangements of N-Allyl-Ynamides

A cascade of Pd-catalyzed N-to-C allyl transfer–intramolecular ketenimine–[2 + 2] cycloadditions of N-allyl ynamides is described. This tandem sequence is highly stereoselective and the [2 + 2] cycloaddition could be rendered in a crossed or fused manner depending on alkene substitutions, leading to...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 12; pp. 3214 - 3217
Main Authors DeKorver, Kyle A, Hsung, Richard P, Song, Wang-Ze, Wang, Xiao-Na, Walton, Mary C
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.06.2012
Amer Chemical Soc
Subjects
Amides - chemistry
Bridged Bicyclo Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Ethylenes - chemistry
Imines - chemistry
Ketones - chemistry
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
CYCLIZATION
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Summary:A cascade of Pd-catalyzed N-to-C allyl transfer–intramolecular ketenimine–[2 + 2] cycloadditions of N-allyl ynamides is described. This tandem sequence is highly stereoselective and the [2 + 2] cycloaddition could be rendered in a crossed or fused manner depending on alkene substitutions, leading to bridged and fused bicycloimines.
Bibliography:NIH RePORTER
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol3013233