Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride

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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 [18F]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-[18F]fluoro-β-alanine in good radiochemical yield.
Original languageEnglish
Issue number1
Pages (from-to) 65–71
Number of pages7
Publication statusPublished - 2015

ID: 125955435