Diastereoselective Additive Trifluoromethylation/Halogenation of Isoxazole Triflones: Synthesis of All-Carbon-Functionalized Trifluoromethyl Isoxazoline Triflones
Version of Record online: 13 FEB 2014
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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Volume 3, Issue 1, pages 14–18, February 2014
How to Cite
Kawai, H., Sugita, Y., Tokunaga, E., Sato, H., Shiro, M. and Shibata, N. (2014), Diastereoselective Additive Trifluoromethylation/Halogenation of Isoxazole Triflones: Synthesis of All-Carbon-Functionalized Trifluoromethyl Isoxazoline Triflones. ChemistryOpen, 3: 14–18. doi: 10.1002/open.201300044
- Issue online: 27 FEB 2014
- Version of Record online: 13 FEB 2014
- Manuscript Received: 24 DEC 2013
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.