Masked 1,3-Dipole Revealed from Aziridines

Double agent: Switching the electronic nature of substituents on an aziridine ring induces the formation of the ring‐opened zwitterionic 1,3‐dipole through CN bond cleavage instead of the usual CC bond cleavage. This novel dipole reacts with alkenes, alkynes, nitriles, and carbonyl compounds to af...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (48), p.9026-9029
Main Authors: Dauban, Philippe, Malik, Guillaume
Format: Article
Language:English
Subjects:
Alkenes - chemistry
aziridines
Aziridines - chemistry
Cellular Biology
Cyclization
cycloaddition
heterocycles
Lewis acids
Life Sciences
Molecular Structure
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Summary:Double agent: Switching the electronic nature of substituents on an aziridine ring induces the formation of the ring‐opened zwitterionic 1,3‐dipole through CN bond cleavage instead of the usual CC bond cleavage. This novel dipole reacts with alkenes, alkynes, nitriles, and carbonyl compounds to afford new types of [3+2] cycloadducts, thereby enhancing the diversity of nitrogen‐containing heterocycles accessible through 1,3‐dipolar cycloadditions. EWG=electron‐withdrawing group.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200904941