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Updated: Apr 15, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride
Christina Schjoeth-Eskesen1, Paul Robert Hansen2, Andreas Kjaer3
1Department of Clinical Physiology, Nuclear Medicine & PET, Copenhagen University Hospital Rigshospitalet Blegdamsvej 9, 2100 Copenhagen Ø (Denmark) ; Department of Clinical Physiology, Nuclear Medicine & PET, Copenhagen University Hospital Rigshospitalet Blegdamsvej 9, 2100 Copenhagen Ø (Denmark).
Abstract:
Aziridines can undergo a range of ring-opening reactions with nucleophiles. The regio- and stereochemistry of the products depend on the substituents on the aziridine. Aziridine ring-opening reactions have rarely been used in radiosynthesis. Herein we report the ring opening of activated aziridine-2-carboxylates with [(18)F]fluoride. The aziridine was activated for nucleophilic attack by substitution of various groups on the aziridine nitrogen atom. Fluorine-18 radiolabelling was followed by ester hydrolysis and removal of the activation group. Totally regioselective ring opening and subsequent deprotection was achieved with tert-butyloxycarbonyl- and carboxybenzyl-activated aziridines to give α-[(18)F]fluoro-β-alanine in good radiochemical yield.
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