Ligand-Free Silver Fluoride-Promoted (3 + 2) Annulation of Oxaziridines and α-Isocyanoacetates: A Diastereoselective Route to <i>cis-</i>Imidazolines
A ligand-free silver fluoride-promoted diastereoselective (3 + 2) annulation reaction between oxaziridines and isocyanoacetates was developed, enabling the efficient synthesis of <i>cis</i>-2-imidazolines under mild conditions (room temperature within 10 min) with up to 90% yield. The resulting <i>cis</i>-imidazolines are readily hydrolyzed to <i>anti</i>-α,β-diamino acid derivatives while maintaining the stereochemical integrity. Additionally, the <i>cis-</i>imidazolines can be efficiently converted to their <i>trans</i> epimers in high yields, providing stereodivergent access to the <i>syn</i>-α,β-diamino acid derivatives.
Authors
- Hu Shi (ORCID: https://orcid.org/0000-0002-5466-5783)
- Siyun Wang (ORCID: https://orcid.org/0000-0003-2468-2483)
- Lixin Zhang (ORCID: https://orcid.org/0000-0003-0894-9520)
- Hui Jin (ORCID: https://orcid.org/0000-0002-7154-5628)
- Jubao Zhou
Institutions
- Shanxi University of Traditional Chinese Medicine (CN)
- Shenyang University of Chemical Technology (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-06-17
- DOI
- https://doi.org/10.1021/acs.joc.5c00592
- Primary Topic
- Synthesis and Catalytic Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Natural Science Foundation of Liaoning Province
- Shenyang University of Chemical Technology