Ag‐Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition of <i>N</i>‐2,2,2‐Trifluoroethylisatin Ketimines with Conjugated Exocyclic Double Bonds: Access to Pyrrolidines with Four Consecutive Stereocenters Including Two Adjacent Spiro‐Quaternary Centers

Abstract Ag‐catalyzed enantioselective 1,3‐dipolar cycloaddition of N ‐2,2,2‐trifluoroethylisatin ketimines with conjugated exocyclic double bonds including α ‐alkylidene succinimides and aurone derivatives was developed for the first time. Using a catalyst system consisting of a ferrocenyl P,N ‐ligand and AgNO 2 , the reaction provides a facile method for the construction of chiral pyrrolidines bearing four consecutive stereocenters and two adjacent spiro‐quaternary chiral centers, as well as offers a direct route to structurally diverse enantioenriched CF 3 ‐containing 3,2′‐pyrrolidinyl spirooxindole derivatives.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2024-09-22
DOI
https://doi.org/10.1002/adsc.202400763
Citations
5
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
1.04
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article

Ag‐Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition of N‐2,2,2‐Trifluoroethylisatin Ketimines with Conjugated Exocyclic Double Bonds: Access to Pyrrolidines with Four Consecutive Stereocenters Including Two Adjacent Spiro‐Quaternary Centers

Ming‐Qiang Zhou, Jian‐Qiang Zhao, Zhen‐Hua Wang, Wei‐Cheng Yuan et al.
5 citations
Advanced Synthesis & Catalysis
Fluorine in Organic Chemistry
1.04
article

Ag‐Catalyzed Asymmetric 1,3‐Dipolar Cycloaddition of N‐2,2,2‐Trifluoroethylisatin Ketimines with Conjugated Exocyclic Double Bonds: Access to Pyrrolidines with Four Consecutive Stereocenters Including Two Adjacent Spiro‐Quaternary Centers

Ming‐Qiang Zhou, Jian‐Qiang Zhao, Zhen‐Hua Wang, Wei‐Cheng Yuan, Lei Yang, Ji‐Hong Liu, Yanping Zhang, Yong You, Jihong Lu
article en
5 citations

Abstract

Abstract Ag‐catalyzed enantioselective 1,3‐dipolar cycloaddition of N ‐2,2,2‐trifluoroethylisatin ketimines with conjugated exocyclic double bonds including α ‐alkylidene succinimides and aurone derivatives was developed for the first time. Using a catalyst system consisting of a ferrocenyl P,N ‐ligand and AgNO 2 , the reaction provides a facile method for the construction of chiral pyrrolidines bearing four consecutive stereocenters and two adjacent spiro‐quaternary chiral centers, as well as offers a direct route to structurally diverse enantioenriched CF 3 ‐containing 3,2′‐pyrrolidinyl spirooxindole derivatives.

Advanced Synthesis & CatalysisVol. 366(24)
Chinese Academy of Sciences (CN), Chengdu Organic Chemicals (China) (CN), Jinhua Academy of Agricultural Sciences (CN), Chengdu University (CN), Institute for Advanced Study (DE), University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 27%
Fluorine in Organic Chemistry
1.04
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