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Trifluoromethylation of Aromatic Isoxazoles: Regio- and Diastereoselective Route to 5-Trifluoromethyl-2-isoxazolines

✍ Scribed by Hiroyuki Kawai; Kentaro Tachi; Etsuko Tokunaga; Dr. Motoo Shiro; Prof. Norio Shibata


Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
297 KB
Volume
123
Category
Article
ISSN
0044-8249

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## Abstract The activation of aromatic, heteroaromatic, or styryl isoxazoles such as (I) or (V) with a nitro group at the 4‐position results in the first diastereoselective trifluoromethylation at the 5‐position by nucleophilic addition of Tms‐CF~3~.

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Ethylenediamine reacted readily with 4ethoxy-1,1,1-trifluoro-3-butene-2-one to form 5-trifliuoromethyl-2,3-dihydro-1,4-diazepine in good yield. Under the same reaction conditions, o-phenylenediamine gave 2-trifluoromethylbenzimidazole and benzimidazole.