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Updated: Jun 18, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Al(OTf)(3)-mediated epoxide ring-opening reactions: toward piperazine-derived physiologically active products
D Bradley G Williams1, Adam Cullen
1Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park 2006, South Africa. bwilliams@uj.ac.za
Abstract:
Al(OTf)(3) is a good catalyst for the ring opening of epoxides, forming beta-amino alcohols bearing the piperazine motif. Two different strategies were examined, where the glycidyl ether resided on one-half of the molecule or the other, allowing insight into a best-case approach for the ring-opening step. Each half of the molecule contained an heteroatom that could be used either to attach the glycidyl moiety or as the nucleophile in the ring-opening reaction, for the same set of reagents, allowing this approach.
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