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
Hauptverfasser: Zhang, Xiang-Zhi, Gan, Kang-Ji, Liu, Xiao-Xue, Deng, Yu-Hua, Wang, Fang-Xin, Yu, Ke-Yin, Zhang, Jing, Fan, Chun-An
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Sprache:eng
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01331