Palladium-Catalyzed Decarboxylative Intramolecular Aziridination from 4H-Isoxazol-5-ones Leading to 1-Azabicyclo[3.1.0]hex-2-enes

Palladium-Catalyzed Decarboxylative Intramolecular Aziridination from 4H-Isoxazol-5-ones Leading to 1-Azabicyclo[3.1.0]hex-2-enes

A decarboxylative intramolecular aziridination reaction of alkene‐tethered 4H‐isoxazol‐5‐ones with a palladium/phosphine catalyst gave 1‐azabicyclo[3.1.0]hex‐2‐enes in moderate to high yields (see scheme; dba=dibenzylideneacetone). The resulting N‐fused bicyclic aziridines readily reacted with vario...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-11, Vol.50 (48), p.11470-11473
Hauptverfasser: Okamoto, Kazuhiro, Oda, Tomohiro, Kohigashi, Sho, Ohe, Kouichi
Format: Artikel
Sprache:eng
Schlagworte:
4H-isoxazol-5-ones
cyclization
decarboxylation
homogeneous catalysis
palladium
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Zusammenfassung:A decarboxylative intramolecular aziridination reaction of alkene‐tethered 4H‐isoxazol‐5‐ones with a palladium/phosphine catalyst gave 1‐azabicyclo[3.1.0]hex‐2‐enes in moderate to high yields (see scheme; dba=dibenzylideneacetone). The resulting N‐fused bicyclic aziridines readily reacted with various reagents to afford ring‐opening pyrroline derivatives.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201105153