Copper-catalyzed synthesis of trisubstituted isoxazoles via a cascade cyclization-migration process.

Masafumi Ueda, Shoichi Sugita, Aoi Sato, Tetsuya Miyoshi, Okiko Miyata

Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.

The Journal of organic chemistry 2012 Oct 19

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An atom-economical, catalytic, and regioselective synthesis of 3,4,5-trisubstituted isoxazoles has been successfully developed. Treatment of O-arylmethyl alkynyl oxime ethers with 5 mol % of Cu(OTf)(2) in chlorobenzene at reflux gave 4-arylmethylisoxazoles in good to excellent yields via the sequential intramolecular addition of the oxime moiety to the alkyne with subsequent 1,3-migration of the arylmethyl group.

Citation

Masafumi Ueda, Shoichi Sugita, Aoi Sato, Tetsuya Miyoshi, Okiko Miyata. Copper-catalyzed synthesis of trisubstituted isoxazoles via a cascade cyclization-migration process. The Journal of organic chemistry. 2012 Oct 19;77(20):9344-51