scholarly journals Photoinduced decarboxylative azidation of cyclic amino acids

2019 ◽  
Vol 17 (7) ◽  
pp. 1839-1842 ◽  
Author(s):  
David C. Marcote ◽  
Rosie Street-Jeakings ◽  
Elizabeth Dauncey ◽  
James J. Douglas ◽  
Alessandro Ruffoni ◽  
...  
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Photoredox Catalysis ◽  
Cyclic Amino Acids

The direct decarboxylative azidation of cyclic α-amino acids has been achieved via visible light-mediated organo-photoredox catalysis.

Recent Advances in Photoredox Catalysis Enabled Functionalization of α-Amino Acids and Peptides: Concepts, Strategies and Mechanisms

Synthesis ◽  
2019 ◽  
Vol 51 (14) ◽  
pp. 2759-2791 ◽  
Author(s):  
Jian-Quan Liu ◽  
Andrey Shatskiy ◽  
Bryan S. Matsuura ◽  
Markus D. Kärkäs
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Hypervalent Iodine ◽  
Amino Acid Residues ◽  
Photoredox Catalysis ◽  
Metal Catalysis ◽  
Specific Amino Acid ◽  
Recent Advances ◽  
Redox Active ◽  
Decarboxylative Coupling

The selective modification of α-amino acids and peptides constitutes a pivotal arena for accessing new peptide-based materials and therapeutics. In recent years, visible light photoredox catalysis has appeared as a powerful platform for the activation of small molecules via single-electron transfer events, allowing previously inaccessible reaction pathways to be explored. This review outlines the recent advances, mechanistic underpinnings, and opportunities of applying photoredox catalysis to the expansion of the synthetic repertoire for the modification of specific amino acid residues.1 Introduction2 Visible-Light-Mediated Functionalization of α-Amino Acids2.1 Decarboxylative Functionalization Involving Redox-Active Esters2.2 Direct Decarboxylative Coupling Strategies2.3 Hypervalent Iodine Reagents2.4 Dual Photoredox and Transition-Metal Catalysis2.5 Amination and Deamination Strategies3 Photoinduced Peptide Diversification3.1 Gese-Type Bioconjugation Methods3.2 Peptide Macrocyclization through Photoredox Catalysis3.3 Biomolecule Conjugation through Arylation3.4 C–H Functionalization Manifolds4 Conclusions and Outlook

Visible-Light-Mediated Synthesis of Oxidized Amides via Organic Photoredox Catalysis

Synthesis ◽  
2018 ◽  
Vol 50 (17) ◽  
pp. 3379-3386 ◽  
Author(s):  
Ting Wang ◽  
Yuliu Du ◽  
Zheng Wei
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Functional Groups ◽  
Photoredox Catalysis ◽  
Reaction Conditions

The development of visible-light-mediated synthesis of oxidized amides is reported. The reaction shows a broad substrate scope and highlights a mild nature of the reaction conditions. A range of functional groups are well tolerated in the reaction. Relying on the strategy, a variety of α-alkoxy amino acids are synthesized.

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acid Derivatives through Photoredox Catalysis

2021 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Elena Vladimirovna Stepanova ◽  
Jian-Quan Liu ◽  
Temerdashev Azamat ◽  
...  
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Visible Light ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Radical Addition ◽  
Amino Acid Derivatives ◽  
Photoredox Catalysis

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived N-sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids....

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

Use of hydrolases for the synthesis of cyclic amino acids

Tetrahedron ◽  
2004 ◽  
Vol 60 (3) ◽  
pp. 717-728 ◽  
Author(s):  
Richard C Lloyd ◽  
Michael C Lloyd ◽  
Mark E.B Smith ◽  
Karen E Holt ◽  
Jonathan P Swift ◽  
...  
Keyword(s):  
Amino Acids ◽  
Cyclic Amino Acids

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

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