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

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride. / Schjøth-Eskesen, Christina; Hansen, Paul Robert; Kjær, Andreas; Gillings, Nic.

In: ChemistryOpen, Vol. 4, No. 1, 2015, p. 65–71.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Schjøth-Eskesen, C, Hansen, PR, Kjær, A & Gillings, N 2015, 'Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride', ChemistryOpen, vol. 4, no. 1, pp. 65–71. https://doi.org/10.1002/open.201402081

APA

Schjøth-Eskesen, C., Hansen, P. R., Kjær, A., & Gillings, N. (2015). Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride. ChemistryOpen, 4(1), 65–71. https://doi.org/10.1002/open.201402081

Vancouver

Schjøth-Eskesen C, Hansen PR, Kjær A, Gillings N. Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride. ChemistryOpen. 2015;4(1): 65–71. https://doi.org/10.1002/open.201402081

Author

Schjøth-Eskesen, Christina ; Hansen, Paul Robert ; Kjær, Andreas ; Gillings, Nic. / Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride. In: ChemistryOpen. 2015 ; Vol. 4, No. 1. pp. 65–71.

Bibtex

@article{64efbfbe4a7c420d839fbbd1ea7239af,
title = "Efficient, regioselective ring-opening of activated aziridine-2-carboxylates with [18F]fluoride",
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 [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.",
author = "Christina Schj{\o}th-Eskesen and Hansen, {Paul Robert} and Andreas Kj{\ae}r and Nic Gillings",
year = "2015",
doi = "10.1002/open.201402081",
language = "English",
volume = "4",
pages = " 65–71",
journal = "ChemistryOpen",
issn = "2191-1363",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "1",

}

RIS

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

Y1 - 2015

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

VL - 4

SP - 65

EP - 71

JO - ChemistryOpen

JF - ChemistryOpen

SN - 2191-1363

IS - 1

ER -

ID: 125955435