Access to Multisubstituted 2(5H)‑Furanones Using Hydrogen Bonding-Promoted Ring-Closing Metathesis and Polyamine Workup

Structurally complex 2­(5H)-furanones are potentially challenging targets for ring-closing metathesis (RCM). A hydrogen bonding-guided RCM strategy was developed in this study to provide 3-substituted and 3,4-disubstituted 2­(5H)-furanones in moderate to high yields with broad functional group toler...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2019-03, Vol.84 (6), p.3419-3430
Hauptverfasser: Tan, Kai, Yan, Huan, Lu, Pengbo, Liu, Yuehui, Ji, Ruigeng, Liu, Zhongxian, Li, Ya-Min, Yu, Fu-Chao, Shen, Yuehai
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Structurally complex 2­(5H)-furanones are potentially challenging targets for ring-closing metathesis (RCM). A hydrogen bonding-guided RCM strategy was developed in this study to provide 3-substituted and 3,4-disubstituted 2­(5H)-furanones in moderate to high yields with broad functional group tolerance. A workup procedure using ethylenediamine-derived polyamines such as tetraethylenepentylamine was also established to effectively remove Ru residues in products.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03293