A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime.

Beilstein J Org Chem

BioCIS CNRS, Faculté de Pharmacie, Labex-LERMIT, Univ Paris Sud, 5 rue J. B. Clément, 92290 Châtenay-Malabry, France.

Published: December 2013

Functionalized 3-trifluoromethyl-2-isoxazolines and 3-trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH4 and NiCl2 to yield the corresponding trifluoromethylated γ-amino alcohols.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3869255PMC
http://dx.doi.org/10.3762/bjoc.9.275DOI Listing

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