Synthesis of trisubstituted isoxazoles by palladium(II)-catalyzed cascade cyclization-alkenylation of 2-alkyn-1-one O-methyl oximes.
Zhigang She, Dongyue Niu, Lei Chen, Maria A Gunawan, Xhesika Shanja, William H Hersh, Yu Chen
Department of Chemistry and Biochemistry, Queens College and the Graduate Center of the City University of New York, Flushing, New York 11367, USA.
The Journal of organic chemistry 2012 Apr 6A palladium-catalyzed, cascade 5-endo-dig cyclization-alkenylation synthesis of isoxazoles has been developed. The addition of 1 equiv of n-Bu(4)NBr significantly increases the yield of the desired 4-alkenyl-3,4,5-trisubstituted isoxazoles. A variety of trisubstituted isoxazoles are prepared in moderate to excellent yields. One example of the synthesis of a naphthoisoxazole is reported by a cascade cyclization-alkenylation-Heck reaction.
Citation
Zhigang She, Dongyue Niu, Lei Chen, Maria A Gunawan, Xhesika Shanja, William H Hersh, Yu Chen. Synthesis of trisubstituted isoxazoles by palladium(II)-catalyzed cascade cyclization-alkenylation of 2-alkyn-1-one O-methyl oximes. The Journal of organic chemistry. 2012 Apr 6;77(7):3627-33
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PMID: 22375914
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