Trifluoromethylation of Aromatic Isoxazoles: Regio‐ and Diastereoselective Route to 5‐Trifluoromethyl‐2‐isoxazolines | Zendy

Kawai Hiroyuki | Zendy; Tachi Kentaro | Zendy; Tokunaga Etsuko | Zendy; Shiro Motoo | Zendy; Shibata Norio | Zendy

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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.

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