Trifluoromethylation of Aromatic Isoxazoles: Regio- and Diastereoselective Route to 5-Trifluoromethyl-2-isoxazolines
β Scribed by Hiroyuki Kawai; Kentaro Tachi; Etsuko Tokunaga; Dr. Motoo Shiro; Prof. Norio Shibata
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 280 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0044-8249
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π SIMILAR VOLUMES
## Abstract The activation of aromatic, heteroaromatic, or styryl isoxazoles such as (I) or (V) with a nitro group at the 4βposition results in the first diastereoselective trifluoromethylation at the 5βposition by nucleophilic addition of TmsβCF~3~.
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.