Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers

Direct Synthesis of Trisubstituted Isoxazoles through Gold-Catalyzed Domino Reaction of Alkynyl Oxime Ethers

Alkynyl oxime ether underwent a gold-catalyzed domino reaction involving cyclization and subsequent Claisen-type rearrangement to afford trisubstituted isoxazoles in a direct, efficient, and regioselective manner. The products were successfully applied to the synthesis of unusual heterocycles as an...

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Veröffentlicht in:Organic letters 2010-06, Vol.12 (11), p.2594-2597
Hauptverfasser: Ueda, Masafumi, Sato, Aoi, Ikeda, Yuki, Miyoshi, Tetsuya, Naito, Takeaki, Miyata, Okiko
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclization
Ethers - chemistry
Gold - chemistry
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Oximes - chemistry
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Zusammenfassung:Alkynyl oxime ether underwent a gold-catalyzed domino reaction involving cyclization and subsequent Claisen-type rearrangement to afford trisubstituted isoxazoles in a direct, efficient, and regioselective manner. The products were successfully applied to the synthesis of unusual heterocycles as an illustration of the potential utility of the reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol100803e