Carbocyclization Cascades of Allyl Ketenimines via Aza-Claisen Rearrangements of N-Phosphoryl-N-allyl-ynamides

A series of carbocyclization cascades of allyl ketenimines initiated through a thermal aza-Claisen rearrangement of N-phosphoryl-N-allyl ynamides is described. Interceptions of the cationic intermediate via Meerwein–Wagner rearrangements and polyene-type cyclizations en route to fused bi- and tricyc...

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Bibliographic Details
Published in:Organic letters 2012-04, Vol.14 (7), p.1768-1771
Main Authors: DeKorver, Kyle A, Wang, Xiao-Na, Walton, Mary C, Hsung, Richard P
Format: Article
Language:English
Subjects:
Allyl Compounds - chemistry
Amides - chemistry
Aza Compounds - chemistry
Catalysis
Cyclization
Imines - chemistry
Molecular Structure
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Summary:A series of carbocyclization cascades of allyl ketenimines initiated through a thermal aza-Claisen rearrangement of N-phosphoryl-N-allyl ynamides is described. Interceptions of the cationic intermediate via Meerwein–Wagner rearrangements and polyene-type cyclizations en route to fused bi- and tricyclic frameworks are featured.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol300366e