Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p-Quinone Methides
Diastereoselective Synthesis of Tetrahydroquinolines Bearing Oxindole Scaffolds via Annulation of in Situ Generated p-Quinone Methides
复制标题
通过原位生成的对醌甲基化物非对映选择性合成带有羟吲哚支架的四氢喹啉
DOI：
10.1002/adsc.202000436
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发表时间：
2020
影响因子：
5.4
通讯作者：
Hu Lihong
中科院分区：
文献类型：
--
作者：
Wang Junwei;Zhao Lei;Zhao Lin;Pan Xiang;Lv Cheng;Zhi Ying;Wang Ai;Zhao Kun;Hu Lihong
在原位生成的对醌类化合物和isatin衍生的烯酸酯之间建立了非对映选择性[4+2]环化反应。在二氧化锰作为氧化剂的情况下，可以很容易地原位生成多种甲苯苯基取代的甲基醌中间体。在没有预先制备p - QMs的情况下，这种前所未有的级联反应在温和的条件下有效地进行，为以高产量合成含有3,3′-螺霉哚支架的4 -苯基取代的四氢喹啉提供了一条简单的途径。
A diastereoselective [4+2] annulation reaction between in situ generatedp‐quinone methides and isatin‐derived enoates has been developed. In the presence of manganese dioxide as an oxidant, a variety of tosylaminophenyl‐substitutedp‐quinone methide intermediates can be readily generated in an in situ fashion. Without pre‐preparation ofp‐QMs, this unprecedented cascade reaction proceeds efficiently under mild conditions, providing a straightforward route to synthesize 4‐phenyl‐substituted tetrahydroquinolines bearing 3,3’‐spirooxindole scaffolds in good yields.