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Leveraging Environmental Control for Regiodivergent Epoxide Ring-Openings.
Anushka Asurumunige1, Sebastian M Malespini1, Tish Huynh1,2
1Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269, United States.
The Journal of Organic Chemistry
|January 2, 2026
Summary
Reaction conditions control chemical synthesis outcomes. This study shows how manipulating environmental factors like catalysts and solvents can precisely direct regioselective epoxide aminolysis, creating valuable beta-amino alcohols.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Reaction environment significantly influences chemical reaction efficiency and selectivity.
- Epoxide aminolysis forms beta-amino alcohols, crucial scaffolds in pharmaceuticals and materials.
- Regioselective synthesis is key for generating specific constitutional isomers.
Purpose of the Study:
- To investigate the impact of environmental parameters on epoxide aminolysis regioselectivity.
- To demonstrate dynamic control over regioisomeric outcomes by manipulating reaction conditions.
- To explore strategies for overriding inherent substrate-controlled selectivity.
Main Methods:
- Utilized epoxide aminolysis as a model system for studying regioselectivity.
- Systematically varied environmental factors: Lewis acid catalyst, solvent, temperature, and stoichiometry.
- Analyzed the formation of constitutional isomers resulting from SN1- or SN2-type pathways.
Main Results:
- Demonstrated that environmental tuning can override intrinsic regioselectivity of epoxide aminolysis.
- Achieved divergent regioselective syntheses by precisely controlling reaction parameters.
- Showcased the ability to dynamically influence the formation of specific regioisomers.
Conclusions:
- Reaction environment engineering is a powerful tool for controlling selectivity in chemical transformations.
- Findings offer new strategies for optimizing reaction conditions and designing predictive models.
- Highlights potential for machine-learning applications in regioselective synthesis.
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