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Schjoeth-Eskesen C, Hansen PR, Kjaer A, et al. Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride. ChemistryOpen. 2014;4(1):65-71doi: 10.1002/open.201402081.
Schjoeth-Eskesen, C., Hansen, P. R., Kjaer, A., & Gillings, N. (2015). Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride. ChemistryOpen, 4(1), 65-71. https://doi.org/10.1002/open.201402081
Schjoeth-Eskesen, Christina, et al. "Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride." ChemistryOpen vol. 4,1 (2015): 65-71. doi: https://doi.org/10.1002/open.201402081
Schjoeth-Eskesen C, Hansen PR, Kjaer A, Gillings N. Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride. ChemistryOpen. 2015 Feb;4(1):65-71. doi: 10.1002/open.201402081. Epub 2014 Nov 21. PMID: 25861572; PMCID: PMC4380955.
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ChemistryOpen. 2015 Feb;4(1):65-71. doi: 10.1002/open.201402081. Epub 2014 Nov 21.

Efficient regioselective ring opening of activated aziridine-2-carboxylates with [(18)f]fluoride.

ChemistryOpen

Christina Schjoeth-Eskesen, Paul Robert Hansen, Andreas Kjaer, Nic Gillings

Affiliations

  1. Department 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).
  2. Department of Drug Design & Pharmacology, University of Copenhagen Universitetsparken 2, 2100 Copenhagen Ø (Denmark).
  3. Department of Clinical Physiology, Nuclear Medicine & PET, Copenhagen University Hospital Rigshospitalet Blegdamsvej 9, 2100 Copenhagen Ø (Denmark) ; Cluster for Molecular Imaging, Faculty of Health Sciences, University of Copenhagen Blegdamsvej 3B, 2100 Copenhagen Ø (Denmark).
  4. Department of Clinical Physiology, Nuclear Medicine & PET, Copenhagen University Hospital Rigshospitalet Blegdamsvej 9, 2100 Copenhagen Ø (Denmark).

PMID: 25861572 PMCID: PMC4380955 DOI: 10.1002/open.201402081

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.

Keywords: aziridines; fluorine-18; radiochemistry; regioselectivity; ring opening

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