Synthesis of 3,4,5-Trisubstituted Isoxazoles through Gold-Catalyzed Cascade Cyclization−Oxidative Alkynylation and Cyclization-Fluorination of 2-Alkynone O-Methyloximes 


Vol. 35,  No. 9, pp. 2635-2644, Sep.  2014
10.5012/bkcs.2014.35.9.2635


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  Abstract

Gold-catalyzed tandem cyclization−oxidative alkynylation and cyclization-fluorination reactions of 2- alkynone O-methyloximes are described. The reactions proceed smoothly at room temperature in the presence of 10 mol % of (PPh3)AuNTf2, 2.5 equivalents of selectfluor, and 2 equivalents of K3PO4. 2-Alkynone Omethyloximes undergo intramolecular oxyauration/cyclization and ensuing oxidative cross-coupling and fluorination process to afford the corresponding 3,4,5-trisubstituted isoxazoles in a cascade manner.

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  Cite this article

[IEEE Style]

D. Song and J. Ryu, "Synthesis of 3,4,5-Trisubstituted Isoxazoles through Gold-Catalyzed Cascade Cyclization−Oxidative Alkynylation and Cyclization-Fluorination of 2-Alkynone O-Methyloximes," Bulletin of the Korean Chemical Society, vol. 35, no. 9, pp. 2635-2644, 2014. DOI: 10.5012/bkcs.2014.35.9.2635.

[ACM Style]

Doo-Hee Song and Jae-Sang Ryu. 2014. Synthesis of 3,4,5-Trisubstituted Isoxazoles through Gold-Catalyzed Cascade Cyclization−Oxidative Alkynylation and Cyclization-Fluorination of 2-Alkynone O-Methyloximes. Bulletin of the Korean Chemical Society, 35, 9, (2014), 2635-2644. DOI: 10.5012/bkcs.2014.35.9.2635.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949