Exploration of A New Zwitterion: Phosphine‐Catalyzed [2+1+2] Cycloaddition Reaction,Advanced Synthesis & Catalysis

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Exploration of A New Zwitterion: Phosphine‐Catalyzed [2+1+2] Cycloaddition Reaction
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2017-04-19 , DOI: 10.1002/adsc.201700242
Yu-Ning Gao ₁ , Qin Xu ₁ , Yin Wei ₂ , Min Shi _{1,

2,

3}

Affiliation

A new zwitterion generated from different electron‐deficient alkenes and phosphines has been designed and its reactivity was explored. We demonstrated that this new zwitterion directed a novel [2+1+2] cycloaddition reaction between vinylpyridines and isatin‐derived electron‐deficient alkenes, affording spirocyclopenteneoxindole derivatives containing three stereocenters in moderate to good yields with good diastereoselectivities. A plausible mechanism has been proposed relying on preliminary mechanistic investigations and supported by theoretical calculations.

中文翻译：

新型两性离子的研究：膦催化的[2 + 1 + 2]环加成反应

设计了一种由不同的缺电子烯烃和膦生成的新型两性离子，并对其反应性进行了研究。我们证明了这种新的两性离子在乙烯基吡啶和伊斯汀衍生的缺电子的烯烃之间进行了新颖的[2 + 1 + 2]环加成反应，从而提供了具有三个立体中心的螺环戊烯氧吲哚衍生物，具有中等至良好的收率，并具有良好的非对映选择性。已经提出了一种可行的机制，该机制依靠初步的机械研究并得到理论计算的支持。

更新日期：2017-04-19

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