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Updated: May 16, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
An unusual silicon mediated transannular cyclopropanation
Bing You1, Kate Hamer, William Lewis
1School of Chemistry, University of Nottingham, University Park, UK.
Researchers report a novel silicon-mediated reaction where a homoallylic nucleophile undergoes intramolecular conjugate addition, forming cyclopropanes. This method utilizes fluoride to transform dihydroazocinones into bicyclic compounds, expanding silicon chemistry.
Area of Science:
- Organic Chemistry
- Organosilicon Chemistry
Background:
- Intramolecular conjugate addition reactions are crucial for carbocyclic and heterocyclic synthesis.
- Silicon-mediated reactions offer unique pathways for bond formation and functionalization.
Purpose of the Study:
- To report a novel silicon-mediated intramolecular 1,4-conjugate addition reaction.
- To achieve cyclopropanation via this methodology.
- To explore the reactivity of silyl groups in complex molecular architectures.
Main Methods:
- Treatment of 6-trimethylsilyl-5,6-dihydroazocinones with a fluoride source.
- Utilizing silicon's unique electronic properties to mediate the reaction.
Main Results:
- Successful intramolecular 1,4-conjugate addition of a homoallylic carbon nucleophile.
- Formation of 4-azabicyclo(5.1.0)octenones through cyclopropanation.
- Demonstration of an unusual extension of silyl group reactivity.
Conclusions:
- The developed method provides an efficient route to cyclopropanated bicyclic lactams.
- This work highlights the synthetic utility of silicon in promoting challenging organic transformations.
- The findings expand the known scope of organosilicon mediated reactions.
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