用于制备手性二取代羟吲哚的3-(3-羟基-1-吡唑-1-基)羟吲哚与β-硝基苯乙烯之间的有机催化对映选择性迈克尔加成反应
Organocatalytic Enantioselective Michael Addition between 3-(3-hydroxy-1-pyrazol-1-yl)Oxindole and βNitrostyrene for the Preparation of Chiral Disubstituted Oxindoles.
作者信息
Song Xiang-Jia, Ren Hong-Xia, Xiang Min, Li Chen-Yi, Zou Ying, Li Xia, Huang Zhi-Cheng, Tian Fang, Wang Li-Xin
机构信息
Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, P.R. China.
University of Chinese Academy of Sciences, Beijing 100039, P.R. China.
出版信息
J Org Chem. 2020 Jul 17;85(14):9290-9300. doi: 10.1021/acs.joc.9b03337. Epub 2020 Jul 6.
A new enantioselective Michael addition between 3-(3-hydroxy-1-pyrazol-1-yl)oxindole, a new synthon generated from isatin ,-cyclic azomethine imine 1,3-dipole, and β-nitrostyrene has been disclosed. A series of chiral 3-(3-oxo-2,3-dihydro-1-pyrazol-1-yl) disubstituted oxindoles were obtained in excellent results (up to 97% yield, up to 94% ee) with moderate to good diastereoselectivities (up to 4.3:1 dr).
已公开了一种新的对映选择性迈克尔加成反应，该反应发生在由异吲哚酮生成的新型合成子3-(3-羟基-1-吡唑-1-基)氧化吲哚、环状甲亚胺亚胺1,3-偶极与β-硝基苯乙烯之间。一系列手性3-(3-氧代-2,3-二氢-1-吡唑-1-基)二取代氧化吲哚以优异的结果（产率高达97%，对映体过量率高达94%）以及中等至良好的非对映选择性（非对映体比例高达4.3:1）获得。
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