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.

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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

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article

Ligand-Free Silver Fluoride-Promoted (3 + 2) Annulation of Oxaziridines and α-Isocyanoacetates: A Diastereoselective Route to cis-Imidazolines

Hu Shi, Siyun Wang, Lixin Zhang, Hui Jin et al.
1 links
The Journal of Organic Chemistry
Synthesis and Catalytic Reactions
article

Ligand-Free Silver Fluoride-Promoted (3 + 2) Annulation of Oxaziridines and α-Isocyanoacetates: A Diastereoselective Route to cis-Imidazolines

Hu Shi, Siyun Wang, Lixin Zhang, Hui Jin, Jubao Zhou
article en

Abstract

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.

The Journal of Organic ChemistryVol. 90(25)
Shanxi University of Traditional Chinese Medicine (CN), Shenyang University of Chemical Technology (CN)
Natural Science Foundation of Liaoning Province, Shenyang University of Chemical Technology
Openalex Percentile: Top 89%
Synthesis and Catalytic Reactions
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Ligand-Free Silver Fluoride-Promoted (3 + 2) Annulation of Oxaziridines and α-Isocyanoacetates: A Diastereoselective Route to <i>cis-</i>Imidazolines — Hu Shi, Siyun Wang, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS