NDLI: A rapid and highly enantioselective C–<sup>11</sup>C bond formation of l-[<sup>11</sup>C]phenylalanine via chiral phase-transfer catalysis

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Organic & Biomolecular Chemistry Vol - 15 Issue - 2

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A rapid and highly enantioselective C–¹¹C bond formation of l-[¹¹C]phenylalanine via chiral phase-transfer catalysis

Content Provider	Royal Society of Chemistry (RSC)
Author	Škrinjar, Janja Windhorst, Albert D. Poot, Alex J. Pekošak, Aleksandra Filp, Ulrike
Copyright Year	2017
Abstract	A rapid method for the synthesis of carbon-11 radiolabeled phenylalanine was developed using a chiral phase-transfer catalyst and a sub-nanomolar quantity of [11C]benzyl iodide as a radio-precursor. Based on a reported synthesis of [11C]benzyl iodide, a Schiff base precursor was evaluated for stereoselective [11C]benzylation. Extensive and interactive screening of the precursor, catalyst, base, stirring and temperature was required to achieve high stereoinduction. The result is an efficient 5-step radiolabeling method to reliably synthesize L- or D-[11C]phenylalanine with an excellent enantiomeric excess of >90% and almost quantitative radiochemical conversion of >95% (n > 5). Additionally, a phase-transfer catalyzed alkylation was utilized on the preparative scale using automated platform. The application resulted in high specific activity ranging from 85–135 GBq μmol−1 of the enantiomerically pure [11C]phenylalanine, showing that the process is robust and amenable to broad use in PET.
Starting Page	570
Ending Page	575
Page Count	6
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	15
Issue Number	3
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c6ob02633h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Schiff base Stereoselectivity Benzyl iodide Phenylalanine Chirality Schiff Phase-transfer catalyst Enantiomeric excess Isotopes of carbon Positron emission tomography Radioactive tracer
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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A rapid and highly enantioselective C–¹¹C bond formation of l-[¹¹C]phenylalanine via chiral phase-transfer catalysis

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