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Related Experiment Video

Updated: Jan 22, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

Ring-Opening of Aziridines Using Tethered Hemiketals.

Raju Silver¹, Abhijit Manna¹, Steven P Kelley²

¹Department of Medicinal Chemistry, University of Kansas, Lawrence, Kansas 66047, United States.

The Journal of Organic Chemistry

|January 21, 2026

Summary

This study introduces novel aziridine ring-opening reactions using pendant hemiketal tethers formed from ketone solvents. These reactions are Lewis acid-catalyzed and offer a new pathway for synthesizing valuable chemical intermediates.

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Covalent Fragment Screening Using the Quantitative Irreversible Tethering Assay

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Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Aziridines are strained three-membered heterocycles crucial in organic synthesis.
Developing efficient methods for aziridine ring-opening is essential for accessing diverse molecular architectures.

Purpose of the Study:

To report the first instance of aziridine ring-opening reactions facilitated by pendant hemiketal tethers.
To explore the utility of ketone solvents in forming these reactive tethers.

Main Methods:

Utilizing catalytic amounts of triphenylcarbenium tetrafluoroborate as a Lewis acid catalyst.
Conducting reactions at room temperature with various ketone solvents like acetone, cyclopentanone, and cyclobutanone.

Main Results:

Successful aziridine ring-opening reactions were achieved via intramolecular attack of hemiketal tethers.
The hemiketal tethers were generated in situ from the reaction solvent.
A range of functional groups were tolerated, yielding products amenable to further synthetic manipulation.

Conclusions:

Pendant hemiketal tethers provide an effective strategy for aziridine functionalization.
The Lewis acid-catalyzed reaction offers a versatile route to complex molecules from simple starting materials.