A Study of Alkene Disulfonoxylation
Shyam Sathyamoorthi1, Steven P Kelley2
1Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.
Summary
New methods for alkene disulfonoxylation offer convenient, air-stable reactions using a commercial iodine(III) oxidant and sulfonic acid. These protocols yield vicinal or geminal disulfonoxylation products, including sulfonoxylated lactones, with high stereospecificity for syn-products.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Alkene functionalization is crucial in organic synthesis.
- Developing efficient and mild methods for difunctionalization remains an active research area.
Purpose of the Study:
- To develop convenient and broadly applicable protocols for alkene disulfonoxylation.
- To investigate the stereochemical outcomes and substrate scope of the developed reactions.
Main Methods:
- Reactions involve stirring alkene substrates with a commercial iodine(III) oxidant and sulfonic acid in dichloromethane.
- Conditions are ambient temperature, open to air, and do not require moisture exclusion.
Main Results:
- Protocols efficiently yield vicinal disulfonoxylation products, often with syn-stereospecificity.
- Terminal alkenes are optimal substrates, but other patterns are compatible.
- Sulfonoxylated lactones are formed from substrates with appropriately positioned esters.
- Geminal disulfonoxylation is exclusively observed for certain styrenyl alkenes, challenging existing literature assignments.
Conclusions:
- The developed protocols provide a convenient and versatile route to various disulfonoxylation products.
- The findings offer new insights into alkene difunctionalization and correct potential misassignments in related literature.
- These methods expand the synthetic utility of iodine(III) oxidants in organic chemistry.
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