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
复制标题
通过对醌甲基化物的分子内乙烯基 Rauhut-Currier 反应对映选择性合成功能化 4-芳基氢香豆素和 4-芳基氢喹啉-2-酮
DOI：
10.1021/acs.orglett.7b01331
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发表时间：
2017-06-16
期刊：
影响因子：
5.2
通讯作者：
Fan, Chun-An
中科院分区：
文献类型：
--
作者：
Zhang, Xiang-Zhi;Gan, Kang-Ji;Fan, Chun-An
报道了一种在手性胺-膦双功能催化剂作用下，通过对醌甲基化物（p-QMs）的分子内乙烯基Rauhut-Currier反应不对称合成功能化的4-芳基-3，4-二氢香豆素和4-芳基-3，4-二氢喹啉-2-酮的新方法。这种分子内模式的催化对映选择性的1，6-共轭加成的p-QMs已被探索的第一次，提供两种类型的合成重要的杂环的高产率和对映选择性。
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.