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 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....

Key Role of π–π Complex in Diary Cross-Coupling between Aryldiazonium Salts and Arylboronic Acids using Photosensitizer-Free Gold/Photoredox Catalysis

2021 ◽  
Author(s):  
Yanhong Liu ◽  
Rong-Xiu Zhu ◽  
Chengbu Liu ◽  
Dongju Zhang
Keyword(s):  
Dft Calculations ◽  
Visible Light ◽  
Cross Coupling ◽  
Photoredox Catalysis ◽  
Arylboronic Acids ◽  
Type Complex ◽  
Free Gold ◽  
Π Complex ◽  
Td Dft

DFT and TD-DFT calculations were performed to better understand the photosensitizer-free visible-light-mediated Au-catalyzed cross-couplings between aryldiazonium salts and arylboronic acids. The π–π type complex between the aryldiazonium salt and the...

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

Transition metal-free, visible-light-mediated construction of α,β-diamino esters via decarboxylative radical addition at room temperature

2019 ◽  
Vol 6 (13) ◽  
pp. 2245-2249 ◽  
Author(s):  
Guibing Wu ◽  
Jingwen Wang ◽  
Chengyu Liu ◽  
Maolin Sun ◽  
Lei Zhang ◽  
...  
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Radical Addition ◽  
Metal Free ◽  
Radical Coupling

A metal-free photoredox catalyzed decarboxylative radical coupling of free-carboxylic acids and glyoxylic oximes was developed to synthesize α,β-diamino acids.

Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis

2019 ◽  
Vol 6 (18) ◽  
pp. 3224-3227 ◽  
Author(s):  
Lidan Wei ◽  
Chengjuan Wu ◽  
Chen-Ho Tung ◽  
Wenguang Wang ◽  
Zhenghu Xu
Keyword(s):  
Amino Acids ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Mild Conditions ◽  
Cooperative Catalysis

A nickel/visible light photoredox co-catalyzed decarboxylative thiolation reaction of carboxylic acids has been developed. This odorless sulfenylation reaction proceeded well via a nickel/photoredox cooperative catalysis pathway under very mild conditions.

Visible light photoredox catalysis: regioselective radical addition of aminoalkyl radicals to 2,3-allenoates

RSC Advances ◽  
2015 ◽  
Vol 5 (68) ◽  
pp. 55290-55294 ◽  
Author(s):  
Xiaojun Dai ◽  
Renjie Mao ◽  
Baochuan Guan ◽  
Xiaoliang Xu ◽  
Xiaonian Li
Keyword(s):  
Visible Light ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Regioselective Addition

Visible-light-mediated regioselective addition of α-aminoalkyl radicals to 2,3-allenoates catalyzed by a photoredox catalyst was developed. The scope and generality of the substrates were broad.

scholarly journals Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis

2015 ◽  
Vol 127 (47) ◽  
pp. 14272-14275 ◽  
Author(s):  
Giulia Bergonzini ◽  
Carlo Cassani ◽  
Carl-Johan Wallentin
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Photoredox Catalysis ◽  
Aromatic Carboxylic Acids ◽  
Acyl Radicals

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.

Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis

2014 ◽  
Vol 50 (18) ◽  
pp. 2308-2310 ◽  
Author(s):  
Pan Xu ◽  
Ablimit Abdukader ◽  
Kaidong Hu ◽  
Yixiang Cheng ◽  
Chengjian Zhu
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Room Temperature ◽  
Photoredox Catalysis ◽  
Unsaturated Carboxylic Acids

A visible-light-induced decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed.

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