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Literature DB >> 28357423

Polyfluoroarylation of oxazolones: access to non-natural fluorinated amino acids.

Abstract

Herein, conditions are provided for the formation and use of the oxazolone enolate for the nucleophilic substitution of highly fluorinated (hetero)arenes, which after unmasking yield highly fluorinated non-natural amino acids and derivatives. In addition, the properties and chemical behavior of this new class of amino acids are explored. The utility is demonstrated in the one pot synthesis of medicinally relevant 2-aminohydantoins.

Entities: Chemical Disease Gene

Mesh：

Substances：

Year: 2017 PMID： 28357423 PMCID： PMC5549939 DOI： 10.1039/c7cc01606a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

19 in total

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Authors: Jason S Fisk; Robert A Mosey; Jetze J Tepe
Journal: Chem Soc Rev Date: 2007-03-12 Impact factor: 54.564

2. Synthesis of fluorinated building blocks by transition-metal-mediated hydrodefluorination reactions.

Authors: Moritz F Kuehnel; Dieter Lentz; Thomas Braun
Journal: Angew Chem Int Ed Engl Date: 2013-01-25 Impact factor: 15.336

3. Selective perfluoro- and polyfluoroarylation of Meldrum's acid.

Authors: Sameera M Senaweera; Jimmie D Weaver
Journal: J Org Chem Date: 2014-10-15 Impact factor: 4.354

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Authors: A F al-Sayyab; A Lawson
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5. Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives.

Authors: Tianli Wang; Zhaoyuan Yu; Ding Long Hoon; Claire Yan Phee; Yu Lan; Yixin Lu
Journal: J Am Chem Soc Date: 2015-12-15 Impact factor: 15.419

6. Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.

Authors: Sameera Senaweera; Jimmie D Weaver
Journal: J Am Chem Soc Date: 2016-02-18 Impact factor: 15.419

7. Photocatalytic hydrodefluorination: facile access to partially fluorinated aromatics.

Authors: Sameera M Senaweera; Anuradha Singh; Jimmie D Weaver
Journal: J Am Chem Soc Date: 2014-02-18 Impact factor: 15.419

8. Palladium-catalyzed alpha-arylation of azlactones to form quaternary amino acid derivatives.

Authors: Xiaoxiang Liu; John F Hartwig
Journal: Org Lett Date: 2003-05-29 Impact factor: 6.005

9. Precious-Metal-Free Heteroarylation of Azlactones: Direct Synthesis of α-Pyridyl, α-Substituted Amino Acid Derivatives.

Authors: Tarn C Johnson; Stephen P Marsden
Journal: Org Lett Date: 2016-09-30 Impact factor: 6.005

10. Photocatalyst size controls electron and energy transfer: selectable E/Z isomer synthesis via C-F alkenylation.

Authors: A Singh; C J Fennell; J D Weaver
Journal: Chem Sci Date: 2016-07-21 Impact factor: 9.825

4 in total

1. Selective and Scalable Perfluoroarylation of Nitroalkanes.

Authors: Jon I Day; Jimmie D Weaver
Journal: J Org Chem Date: 2017-06-09 Impact factor: 4.354

2. Hydrogen Bond Directed Photocatalytic Hydrodefluorination: Overcoming Electronic Control.

Authors: Mohammad B Khaled; Roukaya K El Mokadem; Jimmie D Weaver
Journal: J Am Chem Soc Date: 2017-09-08 Impact factor: 15.419

Review 3. Perfluoroaryl and Perfluoroheteroaryl Reagents as Emerging New Tools for Peptide Synthesis, Modification and Bioconjugation.

Authors: William D G Brittain; Christopher R Coxon
Journal: Chemistry Date: 2021-12-02 Impact factor: 5.020

Review 4. Synthesis of complex unnatural fluorine-containing amino acids.

Authors: William D G Brittain; Carissa M Lloyd; Steven L Cobb
Journal: J Fluor Chem Date: 2020-11 Impact factor: 2.050

4 in total