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Updated: Dec 22, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Rearrangement of 3-Hydroxyazetidines into 2-Oxazolines
Michele Ruggeri1, Amanda W Dombrowski2, Stevan W Djuric3
1Department of Chemistry, University of Durham, South Road, Durham, Durham DH1 3LE, United Kingdom.
Abstract:
A novel rearrangement sequence of 3-hydroxyazetidines via a Ritter initiated cascade provides highly substituted 2-oxazolines in high yields. The reaction conditions and substrate scope of the transformation have been studied demonstrating the generality of the process. The derived products can also be functionalized in order to undergo further intramolecular cyclization leading to a new class of macrocycle. The final cyclization step was shown to be a transformation amenable to continuous flow processing allowing for a dramatic reduction in the reaction time and simple scale-up.
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