title: Diastereoselective additive trifluoromethylation/halogenation of isoxazole triflones: synthesis of all-carbon-functionalized trifluoromethyl isoxazoline triflones.
abstract: Highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives featuring a triflyl (SO2CF3) group at the 4-position were successfully synthesized via diastereoselective trifluoromethylation and halogenation of isoxazole triflones using the Ruppert- Prakash reagent. The trifluoromethylation is quite general in terms of the substrates including 3,5-diaryl isoxazole triflones and 3-aryl-5-styrylisoxazole triflones to provide products in high yields with excellent diastereoselectivities. The highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives are expected to be a new class of antiparasiticides. Thus the triflyl group both activates isoxazoles and the 4-postion of CF3 adducts, and has a potential biological function.
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan).
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kawai
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan).
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Sugita
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan).
authors.forename: Etsuko
authors.initials: E
authors.lastname: Tokunaga
authors.affiliation: Rigaku Corporation, 3-9-12 Mastubara-cho Akishima, Tokyo 196-8666 (Japan).
authors.forename: Hiroyasu
authors.initials: H
authors.lastname: Sato
authors.affiliation: Rigaku Corporation, 3-9-12 Mastubara-cho Akishima, Tokyo 196-8666 (Japan).
authors.forename: Motoo
authors.initials: M
authors.lastname: Shiro
authors.affiliation: Department of Frontier Materials, Graduate School of Engineering, Nagoya Institute of Technology Gokiso, Showa-ku, Nagoya 466-8555 (Japan).
authors.forename: Norio
authors.initials: N
authors.lastname: Shibata
keywords: agrochemicals; halogenations; isoxazolines; trifluoromethanesulfonyl; trifluoromethylations