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Updated: May 18, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Copper-catalyzed synthesis of trisubstituted isoxazoles via a cascade cyclization-migration process
Masafumi Ueda1, Shoichi Sugita, Aoi Sato
1Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Abstract:
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.
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