51979-01-2Relevant academic research and scientific papers
Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions
Disetti, Paolo,Moccia, Maria,Salazar Illera, Diana,Suresh, Surisetti,Adamo, Mauro F. A.
supporting information, p. 10609 - 10612 (2015/11/17)
The reaction between 3-methyl-4-nitro-5-styrylisoxazoles and ethyl isocyanoacetate proceeded under phase transfer catalysis to give enantioenriched monoadducts in high enantiomeric excess (up to 99% ee). The resulting adducts were subsequently cyclised to give 2,3-dihydropyrroles and substituted pyrrolidines in identical high ees and as a single diastereoisomer.
Trifluoromethylation of aromatic isoxazoles: Regio- and diastereoselective route to 5-trifluoromethyl-2-isoxazolines
Kawai, Hiroyuki,Tachi, Kentaro,Tokunaga, Etsuko,Shiro, Motoo,Shibata, Norio
supporting information; experimental part, p. 7803 - 7806 (2011/10/05)
It all adds up: The activation of aromatic isoxazoles with a nitro group at the 4-position has enabled the first regio- and diastereoselective trifluoromethylation at the 5-position of isoxazoles by nucleophilic addition using Me3SiCF3 (see scheme; DMF=N,N′- dimethylformamide). The process was demonstrated with a broad range of 3,5-aromatic, heteroaromatic and aliphatic substrates.
