Cu(II)-catalyzed regioselective ring-opening of N-tosylazetidines with phenols

Cu(II)-catalyzed regioselective ring-opening of N-tosylazetidines with phenols

An efficient synthesis of γ-amino ethers has been achieved via the ring-opening of 2-aryl N-tosylazetidines with phenols under the catalysis of Cu(OTf)2. This reaction features excellent yields and regioselectivities, low catalyst loading, mild reaction conditions and good scalability. One of the pr...

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Veröffentlicht in:Tetrahedron 2023-02, Vol.132, p.133263, Article 133263
Hauptverfasser: Kan, Xiu-Mei, Zhu, Jie, Li, Pin-Hua, Wu, Zhi-Chuan, Yang, Pei-Jun
Format: Artikel
Sprache:eng
Schlagworte:
1,3-Amino ether
Azetidine
Lewis acid catalysis
Regioselectivity
Ring-opening reaction
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Zusammenfassung:An efficient synthesis of γ-amino ethers has been achieved via the ring-opening of 2-aryl N-tosylazetidines with phenols under the catalysis of Cu(OTf)2. This reaction features excellent yields and regioselectivities, low catalyst loading, mild reaction conditions and good scalability. One of the product was transformed to the drug molecule (±)-fluoxetine via a two-step procedure. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2023.133263