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

TY - JOUR

T1 - Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride

AU - Schjøth-Eskesen, Christina

AU - Hansen, Paul Robert

AU - Kjær, Andreas

AU - Gillings, Nic

PY - 2015/2

Y1 - 2015/2

N2 - 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.

AB - 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.

U2 - 10.1002/open.201402081

DO - 10.1002/open.201402081

M3 - Journal article

C2 - 25861572

SN - 2191-1363

VL - 4

SP - 65

EP - 71

JO - ChemistryOpen

JF - ChemistryOpen

IS - 1

ER -