title: Copper-catalyzed synthesis of trisubstituted isoxazoles via a cascade cyclization-migration process.
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.
authors.affiliation: Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
authors.forename: Masafumi
authors.initials: M
authors.lastname: Ueda
authors.forename: Shoichi
authors.initials: S
authors.lastname: Sugita
authors.forename: Aoi
authors.initials: A
authors.lastname: Sato
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Miyoshi
authors.forename: Okiko
authors.initials: O
authors.lastname: Miyata
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D007555:Isoxazoles; D009942:Organometallic Compounds; D003300:Copper