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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.

SUBMITTER: Kawai H

PROVIDER: S-EPMC3943607 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Diastereoselective additive trifluoromethylation/halogenation of isoxazole triflones: synthesis of all-carbon-functionalized trifluoromethyl isoxazoline triflones.

Kawai Hiroyuki H Sugita Yutaka Y Tokunaga Etsuko E Sato Hiroyasu H Shiro Motoo M Shibata Norio N

ChemistryOpen 20140213 1

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 high ...[more]

PMID: 24688889

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