P(NMe <sub>2</sub> ) <sub>3</sub> -Mediated Reductive (4 + 1) Annulation Reaction of Isatins with Oxindole-Derived α,β-Unsaturated Imines and Diastereoselective Synthesis of 2,3-Di(spirooxindolyl)pyrrolines
Herein, we report a P(NMe<sub>2</sub>)<sub>3</sub>-mediated (4 + 1) annulation reaction between substituted isatins and oxindole-derived α,β-unsaturated imines. This method facilitates the diastereoselective synthesis of a variety of structurally diverse 2,3-di(spirooxindolyl)pyrrolines featuring two vicinal tetrasubstituted carbon-stereocenters in moderate to high yields with exclusive diastereoselectivity. Mechanistically, the reaction is proposed to proceed via a Kukhtin-Ramirez adduct-initiated reductively deoxygenative annulation pathway, comprising an intermolecular nucleophilic 1,4-addition and subsequently followed by an intramolecular stereoselective S<sub>N</sub>2-type substitution. This strategy provides a practical and complementary synthetic approach to forge biologically relevant 2,3-di(spirooxindolyl)pyrrolidine scaffolds from readily accessible starting materials.
Authors
- Chang‐Jiang Yang (ORCID: https://orcid.org/0000-0003-3405-1546)
- Fangna Sun
- Zhengjie He (ORCID: https://orcid.org/0000-0002-7891-0245)
- Lin Liu (ORCID: https://orcid.org/0000-0001-5733-6910)
- Jiesi Luo
- Pei-Jie Huang
Institutions
- Nankai University (CN)
- Dynamic Systems (United States) (US)
- Great Bay University
- Ministry of Industry and Information Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-12-05
- DOI
- https://doi.org/10.1021/acs.joc.5c02507
- Citations
- 1
- Primary Topic
- Asymmetric Synthesis and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.94