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Trifluoromethylation of Aromatic Isoxazoles: Regio‐ and Diastereoselective Route to 5‐Trifluoromethyl‐2‐isoxazolines
Author(s) -
Kawai Hiroyuki,
Tachi Kentaro,
Tokunaga Etsuko,
Shiro Motoo,
Shibata Norio
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201102442
Subject(s) - trifluoromethylation , trifluoromethyl , chemistry , nitro , nucleophile , organic chemistry , catalysis , alkyl
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 Me 3 SiCF 3 (see scheme; DMF= N,N′ ‐dimethylformamide). The process was demonstrated with a broad range of 3,5‐aromatic, heteroaromatic and aliphatic substrates.