Organocatalytic Enantioselective Michael Addition between 3-(3-hydroxy-1H-pyrazol-1-yl)Oxindole and β-Nitrostyrene for the Preparation of Chiral Disubstituted Oxindoles.,The Journal of Organic Chemistry

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Organocatalytic Enantioselective Michael Addition between 3-(3-hydroxy-1H-pyrazol-1-yl)Oxindole and β-Nitrostyrene for the Preparation of Chiral Disubstituted Oxindoles.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-25 , DOI: 10.1021/acs.joc.9b03337
Xiang-Jia Song _{1,

2} , Hong-Xia Ren _{1,

2} , Min Xiang _{1,

2} , Chen-Yi Li _{1,

2} , Ying Zou _{1,

2} , Xia Li _{1,

2} , Zhi-Cheng Huang _{1,

2} , Fang Tian ₁ , Li-Xin Wang ₁

Affiliation

A new enantioselective Michael addition between 3-(3-hydroxy-1H-pyrazol-1-yl)oxindole, a new synthon generated from isatin N,N′-cyclic azomethine imine 1,3-dipole, and β-nitrostyrene has been disclosed. A series of chiral 3-(3-oxo-2,3-dihydro-1H-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).

中文翻译：

3-（3-羟基-1H-吡唑-1-基）O和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，用于制备手性二取代的吲哚。

在3-（3-羟基-1 H-吡唑-1-基）恶吲哚之间的一种新的对映选择性迈克尔加成反应，它是由Isatin N，N'-环偶氮甲亚胺亚胺1,3-偶极和β-硝基苯乙烯生成的新合成子。披露。获得了一系列优异的收率（最高97％，最高94％ee）的手性3-（3-oxo-2,3-dihydro-1 H -pyrazol-1-yl）双取代的吲哚。非对映选择性（达4.3：1 dr）。

更新日期：2020-07-17

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