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...
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Veröffentlicht in: | Journal of organic chemistry 2019-03, Vol.84 (6), p.3419-3430 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b03293 |