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Keywords:

  • agrochemicals;
  • halogenations;
  • isoxazolines;
  • trifluoromethanesulfonyl;
  • trifluoromethylations

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.