Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution

Evgeny V. Revunov; Fedor Zhuravlev

doi:10.1016/j.jfluchem.2013.09.006

Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [¹⁸F]F-MISO via kinetic resolution

Evgeny V. Revunov, Fedor Zhuravlev

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Abstract

The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [18F]HF in a combination with (−)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-18F-fluorohydrines in 78–93% radiochemical yield (RCY) and 20–46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [18F]F-MISO, which took 1.5h and after solid phase-based purification delivered [18F]F-MISO in 81%/45% analytical/preparative RCY and 55% ee.

Original language	English
Journal	Journal of Fluorine Chemistry
Volume	156
Pages (from-to)	130-135
ISSN	0022-1139
DOIs	https://doi.org/10.1016/j.jfluchem.2013.09.006
Publication status	Published - 2013

Keywords

Radiofluorination
Metal mediated
F-MISO
PET
[18F]

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@article{de11e371dcf74c95986c22be5179022b,

title = "Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution",

abstract = "The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [18F]HF in a combination with (−)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-18F-fluorohydrines in 78–93\% radiochemical yield (RCY) and 20–46\% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [18F]F-MISO, which took 1.5h and after solid phase-based purification delivered [18F]F-MISO in 81\%/45\% analytical/preparative RCY and 55\% ee.",

keywords = "Radiofluorination, Metal mediated, F-MISO, PET, [18F]",

author = "Revunov, \{Evgeny V.\} and Fedor Zhuravlev",

year = "2013",

doi = "10.1016/j.jfluchem.2013.09.006",

language = "English",

volume = "156",

pages = "130--135",

journal = "Journal of Fluorine Chemistry",

issn = "0022-1139",

publisher = "Elsevier",

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TY - JOUR

T1 - Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution

AU - Revunov, Evgeny V.

AU - Zhuravlev, Fedor

PY - 2013

Y1 - 2013

N2 - The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [18F]HF in a combination with (−)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-18F-fluorohydrines in 78–93% radiochemical yield (RCY) and 20–46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [18F]F-MISO, which took 1.5h and after solid phase-based purification delivered [18F]F-MISO in 81%/45% analytical/preparative RCY and 55% ee.

AB - The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [18F]HF in a combination with (−)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-18F-fluorohydrines in 78–93% radiochemical yield (RCY) and 20–46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [18F]F-MISO, which took 1.5h and after solid phase-based purification delivered [18F]F-MISO in 81%/45% analytical/preparative RCY and 55% ee.

KW - Radiofluorination

KW - Metal mediated

KW - F-MISO

KW - PET

KW - [18F]

U2 - 10.1016/j.jfluchem.2013.09.006

DO - 10.1016/j.jfluchem.2013.09.006

M3 - Journal article

SN - 0022-1139

VL - 156

SP - 130

EP - 135

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

ER -