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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Inhibiting Isomerization via Confinement in Ice-Water Interfaces Enhances Stereoselectivity in [2 + 2] Cycloaddition.

Shi-Peng Wan^1,2,3, Dan Wang^4,5, Jiahui Wu⁴

¹Beijing National Laboratory for Molecular Science, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Journal of the American Chemical Society

|October 7, 2025

Summary

This summary is machine-generated.

Researchers developed an ice-assisted photochemical method for synthesizing cyclobutanes. This approach prevents reactant isomerization and yields highly stereoselective syn-cyclobutane products, offering a sustainable synthesis route.

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Area of Science:

Organic Chemistry
Photochemistry
Materials Science

Background:

Cyclobutanes are crucial structural units in pharmaceuticals and natural products.
Traditional [2+2] photocycloadditions face challenges with olefin isomerization and stereoselectivity, limiting synthetic utility.

Purpose of the Study:

To develop an efficient and stereoselective method for synthesizing cyclobutane derivatives.
To investigate the role of ice-water interfaces in mediating photochemical reactions.

Main Methods:

Utilizing a confined ice-water interface to mediate [2+2] photocycloadditions.
Employing theoretical simulations and experimental studies to analyze reaction mechanisms.
Investigating the adsorption and arrangement of solute molecules on ice surfaces.

Main Results:

Achieved highly stereoselective synthesis of syn-cyclobutane products (syn-dimer > 95%).
Successfully inhibited rapid cis/trans isomerization of olefin substrates.
Demonstrated the catalytic role of the ice surface in promoting syn-configuration and inhibiting photoisomerization.

Conclusions:

Ice-assisted photochemistry offers an effective strategy for stereoselective cyclobutane synthesis.
The ice-water interface acts as a catalyst by organizing reactants into a prereactive syn-aligned configuration.
This method presents a sustainable and environmentally friendly approach to photochemical synthesis.