Cascade Formation of Isoxazoles: Facile Base-Mediated Rearrangement of Substituted Oxetanes

Cascade Formation of Isoxazoles: Facile Base-Mediated Rearrangement of Substituted Oxetanes

Give me five! Nitro compounds and oxetan‐3‐one react through an intriguing cascade sequence to give isoxazole‐4‐carbaldehydes using inexpensive reagents in a one‐pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3‐substituted isoxazole‐4‐carbaldehydes were obtained in high overall yields....

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Veröffentlicht in:Angewandte Chemie International Edition 2011-05, Vol.50 (23), p.5379-5382
Hauptverfasser: Burkhard, Johannes A., Tchitchanov, Boris H., Carreira, Erick M.
Format: Artikel
Sprache:eng
Schlagworte:
aldehydes
Aldehydes - chemistry
Biological Products - chemical synthesis
Ethers, Cyclic - chemistry
heterocycles
Isoxazoles - chemical synthesis
Molecular Structure
nitro compounds
Nitro Compounds - chemistry
oxetanes
rearrangements
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Zusammenfassung:Give me five! Nitro compounds and oxetan‐3‐one react through an intriguing cascade sequence to give isoxazole‐4‐carbaldehydes using inexpensive reagents in a one‐pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3‐substituted isoxazole‐4‐carbaldehydes were obtained in high overall yields.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100260