Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 29, Pages 6506-6509Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301096
Keywords
Fluorine; Iodine; Heterocycles; Hypervalent compounds; Organocatalysis; N-O coupling
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Funding
- Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan
- MEXT [24105513, 2304]
- Japan Science and Technology (JST) (ACT-C: Creation of Advanced Catalytic Transformation for the Sustainable Manufacturing at Low Energy, Low Environmental Load)
- Grants-in-Aid for Scientific Research [24105513, 2304] Funding Source: KAKEN
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Biologically attractive trifluoromethyl-2-isoxazoline N-oxides were synthesized in good yields for the first time by the [hydroxy(tosyloxy)iodo]benzene-mediated oxidative N-O coupling of -trifluoromethyl -hydroxy ketoximes generated from trifluoromethyl -keto alcohols. The present method allows the synthesis of previously unknown 5-trifluoromethyl-2-isoxazoline N-oxides and also provides an alternative for the enantioselective synthesis of antiparasitic 5-trifluoromethyl-2-isoxazolines by sequential reduction.
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