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Diastereoselective Additive Trifluoromethylation/Halogenation of Isoxazole Triflones: Synthesis of All-Carbon-Functionalized Trifluoromethyl Isoxazoline Triflones

Highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives featuring a triflyl (SO(2)CF(3)) group at the 4-position were successfully synthesized via diastereoselective trifluoromethylation and halogenation of isoxazole triflones using the Ruppert– Prakash reagent. The trifluoromethylation is...

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Detalles Bibliográficos
Autores principales: Kawai, Hiroyuki, Sugita, Yutaka, Tokunaga, Etsuko, Sato, Hiroyasu, Shiro, Motoo, Shibata, Norio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3943607/
https://www.ncbi.nlm.nih.gov/pubmed/24688889
http://dx.doi.org/10.1002/open.201300044
Descripción
Sumario:Highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives featuring a triflyl (SO(2)CF(3)) 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 CF(3) adducts, and has a potential biological function.