Organic Letters
Organic Letters
5 years ago

Enantioselective Synthesis of Functionalized 4-Aryl Hydrocoumarins and 4-Aryl Hydroquinolin-2-ones via Intramolecular Vinylogous Rauhut–Currier Reaction of para-Quinone Methides

Enantioselective Synthesis of Functionalized 4-Aryl Hydrocoumarins and 4-Aryl Hydroquinolin-2-ones via Intramolecular Vinylogous Rauhut–Currier Reaction of para-Quinone Methides
Xiang-Zhi Zhang, Kang-Ji Gan, Jing Zhang, Yu-Hua Deng, Ke-Yin Yu, Xiao-Xue Liu, Chun-An Fan, Fang-Xin Wang
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01331

DOI: 10.1021/acs.orglett.7b01331

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