Enantioselective Synthesis of Functionalized 4‑Aryl Hydrocoumarins and 4‑Aryl Hydroquinolin-2-ones via Intramolecular Vinylogous Rauhut–Currier Reaction of para-Quinone Methides
A novel strategy for the asymmetric construction of functionalized 4-aryl-3,4-dihydrocoumarins and 4-aryl-3,4-dihydroquinolin-2-ones via an intramolecular vinylogous Rauhut–Currier reaction of para-quinone methides (p-QMs) under the bifunctional catalysis of chiral amine-phosphine is described. This...
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Veröffentlicht in: | Organic letters 2017-06, Vol.19 (12), p.3207-3210 |
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Hauptverfasser: | , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A novel strategy for the asymmetric construction of functionalized 4-aryl-3,4-dihydrocoumarins and 4-aryl-3,4-dihydroquinolin-2-ones via an intramolecular vinylogous Rauhut–Currier reaction of para-quinone methides (p-QMs) under the bifunctional catalysis of chiral amine-phosphine is described. This intramolecular mode for the catalytic enantioselective 1,6-conjugate addition of p-QMs has been explored for the first time, delivering two types of synthetically important heterocycles in high yields and enantioselectivites. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.7b01331 |