Intermolecular (5+3) Cycloaddition of Bicyclo[1.1.0]butanes with Oxidopyrylium
Penghui Yan1, Tongxiang Cao1, Shifa Zhu1,2
1Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, P. R. China.
Organic Letters
|February 12, 2026
Summary
This study introduces a novel cycloaddition reaction between bicyclo[1.1.0]butanes and maltol derivatives. It enables efficient synthesis of complex bridged bicyclo[5.1.1]nonanone scaffolds under mild conditions.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Bicyclo[1.1.0]butanes (BCBs) are strained carbocycles with unique reactivity.
- Medium-ring scaffolds are important in medicinal chemistry but challenging to synthesize.
Purpose of the Study:
- To develop a new synthetic route to all-carbon bridged bicyclo[5.1.1]nonanones.
- To explore the cycloaddition of BCBs with oxidopyrylium species.
Main Methods:
- Formal (5+3) cycloaddition reaction.
- Utilized oxidopyrylium species as 1,5-dipoles.
- Employed bicyclo[1.1.0]butanes (BCBs) as reaction partners.
Main Results:
- Successfully synthesized all-carbon bridged bicyclo[5.1.1]nonanones.
- The reaction proceeds under mild conditions.
- Demonstrated high functional group tolerance and broad substrate scope.
Conclusions:
- This work presents a novel and efficient pathway for constructing complex bicyclic scaffolds.
- The developed method offers a valuable tool for synthetic chemists exploring constrained medium-ring systems.
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