Anionic Reactions of N-(trans-2,3-Diphenylaziridin-1-yl)imines and Their Use as 1,1-Dipoles in Anionic Cyclizations

Reaction of N‐(trans‐2,3‐diphenylaziridin‐1‐yl)imines with alkyllithiums and organocuprates afforded the desired addition products after consecutive fragmentations along with liberation of stilbene and nitrogen gas, while the reaction of N‐(2‐phenylaziridin‐1‐yl)imines under similar conditions gave...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2005-10, Vol.347 (11-13), p.1513-1516
Main Authors: Hwang, Jung-ll, Hong, Young-Taek, Kim, Sunggak
Format: Article
Language:English
Subjects:
1,1‐dipoles
1-dipoles
alkyllithiums
anionic cyclizations
aziridines
hydrazones
imines
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Summary:Reaction of N‐(trans‐2,3‐diphenylaziridin‐1‐yl)imines with alkyllithiums and organocuprates afforded the desired addition products after consecutive fragmentations along with liberation of stilbene and nitrogen gas, while the reaction of N‐(2‐phenylaziridin‐1‐yl)imines under similar conditions gave an anomalous by‐product. Anionic cyclizations of N‐(trans‐2,3‐diphenylaziridin‐1‐yl)imines using unactivated alkenes and alkynes as acceptors proceeded smoothly, yielding cyclized products in good yields.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200505110