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Literature DB >> 26360631

Organomediated Enantioselective (18)F Fluorination for PET Applications.

Faye Buckingham¹, Anna K Kirjavainen², Sarita Forsback², Anna Krzyczmonik², Thomas Keller², Ian M Newington³, Matthias Glaser³, Sajinder K Luthra³, Olof Solin², Véronique Gouverneur⁴.

Abstract

The first organomediated asymmetric (18)F fluorination has been accomplished using a chiral imidazolidinone and [(18)F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched (18)F-labeled α-fluoroaldehydes (>90% ee), which are versatile chiral (18)F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[(18)F]fluoroglutamic acid.

Entities: Chemical

Keywords: asymmetric synthesis; enamines; fluorine-18; organocatalysis; positron emission tomography

Mesh：

Substances：

Year: 2015 PMID： 26360631 DOI： 10.1002/anie.201506035

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

9 in total

1. Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

Authors: Hang Shi; Augustin Braun; Lu Wang; Steven H Liang; Neil Vasdev; Tobias Ritter
Journal: Angew Chem Int Ed Engl Date: 2016-08-05 Impact factor: 15.336

2. Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Authors: Xinghua Ma; Mohamed Diane; Glenn Ralph; Christine Chen; Mark R Biscoe
Journal: Angew Chem Int Ed Engl Date: 2017-09-04 Impact factor: 15.336

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

Authors: Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal: Angew Chem Int Ed Engl Date: 2019-01-14 Impact factor: 15.336

4. Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.

Authors: Anna E Hurtley; Elizabeth A Stone; Anthony J Metrano; Scott J Miller
Journal: J Org Chem Date: 2017-11-03 Impact factor: 4.354

Organomediated Enantioselective (18)F Fluorination for PET Applications.

1. Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

2. Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

4. Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.

Review 5. Recent Progress toward Microfluidic Quality Control Testing of Radiopharmaceuticals.

6. Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF₃·Et₂O as the Fluorine Source and Activating Reagent.

7. Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion.

8. Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling.

Review 9. Closing the gap between ¹⁹F and ¹⁸F chemistry.

Organomediated Enantioselective (18)F Fluorination for PET Applications.

1. Synthesis of (18) F-Difluoromethylarenes from Aryl (Pseudo) Halides.

2. Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

4. Desymmetrization of Diarylmethylamido Bis(phenols) through Peptide-Catalyzed Bromination: Enantiodivergence as a Consequence of a 2 amu Alteration at an Achiral Residue within the Catalyst.

Review 5. Recent Progress toward Microfluidic Quality Control Testing of Radiopharmaceuticals.

6. Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF3·Et2O as the Fluorine Source and Activating Reagent.

7. Nucleophilic (Radio)Fluorination of α-Diazocarbonyl Compounds Enabled by Copper-Catalyzed H-F Insertion.

8. Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling.

Review 9. Closing the gap between 19F and 18F chemistry.

Review 3. Chemistry for Positron Emission Tomography: Recent Advances in ¹¹ C-, ¹⁸ F-, ¹³ N-, and ¹⁵ O-Labeling Reactions.

6. Catalytic Synthesis of 5-Fluoro-2-oxazolines: Using BF₃·Et₂O as the Fluorine Source and Activating Reagent.

Review 9. Closing the gap between ¹⁹F and ¹⁸F chemistry.