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.
Authors
- Ming‐Qiang Zhou
- Jian‐Qiang Zhao (ORCID: https://orcid.org/0000-0002-4444-9630)
- Zhen‐Hua Wang (ORCID: https://orcid.org/0000-0002-0603-707X)
- Wei‐Cheng Yuan (ORCID: https://orcid.org/0000-0003-4850-8981)
- Lei Yang (ORCID: https://orcid.org/0000-0001-9172-0879)
- Ji‐Hong Liu (ORCID: https://orcid.org/0000-0001-6686-1629)
- Yanping Zhang (ORCID: https://orcid.org/0000-0002-4190-7026)
- Yong You (ORCID: https://orcid.org/0000-0002-4689-0235)
- Jihong Lu
Institutions
- 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)
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