scholarly journals A mechanochemical approach to access the proline–proline diketopiperazine framework

2017 ◽  
Vol 13 ◽  
pp. 2169-2178 ◽  
Author(s):  
Nicolas Pétry ◽  
Hafid Benakki ◽  
Eric Clot ◽  
Pascal Retailleau ◽  
Farhate Guenoun ◽  
...  
Keyword(s):  
Amino Acid ◽  
Dft Calculations ◽  
Nucleophilic Substitution ◽  
Ball Milling ◽  
Building Block ◽  
Ball Mill ◽  
Amino Acid Derivatives ◽  
Solvent Free Conditions ◽  
Proline Amino Acid ◽  
High Stereoselectivity

Ball milling was exploited to prepare a substituted proline building block by mechanochemical nucleophilic substitution. Subsequently, the mechanocoupling of hindered proline amino acid derivatives was developed to provide proline–proline dipeptides under solvent-free conditions. A deprotection–cyclization sequence yielded the corresponding diketopiperazines that were obtained with a high stereoselectivity which could be explained by DFT calculations. Using this method, an enantiopure disubstituted Pro–Pro diketopiperazine was synthesized in 4 steps, making 5 new bonds using a ball mill.

UV-Light-Induced Dehydrogenative N-Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

Synthesis ◽  
2022 ◽  
Author(s):  
Dishu Zeng ◽  
Tianbao Yang ◽  
Niu Tang ◽  
Wei Deng ◽  
Jiannan Xiang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Organic Synthesis ◽  
Efficient Method ◽  
Building Block ◽  
Room Temperature ◽  
Uv Light ◽  
Amino Acid Derivatives ◽  
One Pot ◽  
Plausible Mechanism ◽  
High Yields

A simple, mild, green and efficient method for the synthesis of 2-aminobenzamides was highly desired in organic synthesis. Herein, we developed an efficient, one-pot strategy for the synthesis of 2-aminobenzamides with high yields irradiated by UV light. 32 examples proceeded successfully by this photo-induced protocol. The yield reached up to 92%. The gram scale was also achieved easily. This building block could be applied in the preparation of quinazolinones derivatives. Amino acid derivatives could be employed smoothly at room temperature. Finally, a plausible mechanism was proposed.

scholarly journals Biomimetic enantioselective synthesis of β,β-difluoro-α-amino acid derivatives

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Qiupeng Peng ◽  
Bingjia Yan ◽  
Fangyi Li ◽  
Ming Lang ◽  
Bei Zhang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Structural Diversity ◽  
Enantioselective Synthesis ◽  
Amino Acid Derivatives ◽  
Proton Shift ◽  
Wide Range ◽  
Fluorine Compounds ◽  
Optically Pure ◽  
High Stereoselectivity ◽  
High Application

AbstractAlthough utilization of fluorine compounds has a long history, synthesis of chiral fluorinated amino acid derivatives with structural diversity and high stereoselectivity is still very appealing and challenging. Here, we report a biomimetic study of enantioselective [1,3]-proton shift of β,β-difluoro-α-imine amides catalyzed by chiral quinine derivatives. A wide range of corresponding β,β-difluoro-α-amino amides were achieved in good yields with high enantioselectivities. The optically pure β,β-difluoro-α-amino acid derivatives were further obtained, which have high application values in the synthesis of fluoro peptides, fluoro amino alcohols and other valuable fluorine-containing molecules.

scholarly journals Gold(iii) tetraarylporphyrin amino acid derivatives: ligand or metal centred redox chemistry?

2016 ◽  
Vol 7 (1) ◽  
pp. 596-610 ◽  
Author(s):  
Sebastian Preiß ◽  
Jascha Melomedov ◽  
Anica Wünsche von Leupoldt ◽  
Katja Heinze
Keyword(s):  
Amino Acid ◽  
Dft Calculations ◽  
Epr Spectroscopy ◽  
Redox Chemistry ◽  
Amino Acid Derivatives

EPR spectroscopy and DFT calculations show that the site of reduction of porphyrinato gold(iii) complexes depends on the counterions X, themesosubstituents R and the solvent.

Asymmetric NHC-Catalyzed Aza-Diels–Alder Reactions: Highly Enantioselective Route to α-Amino Acid Derivatives and DFT Calculations

2014 ◽  
Vol 16 (15) ◽  
pp. 3872-3875 ◽  
Author(s):  
Limin Yang ◽  
Fei Wang ◽  
Richmond Lee ◽  
Yunbo Lv ◽  
Kuo-Wei Huang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Dft Calculations ◽  
Diels Alder ◽  
Amino Acid Derivatives

ChemInform Abstract: Asymmetric NHC-Catalyzed Aza-Diels-Alder Reactions: Highly Enantioselective Route to α-Amino Acid Derivatives and DFT Calculations.

ChemInform ◽  
2015 ◽  
Vol 46 (4) ◽  
pp. no-no
Author(s):  
Limin Yang ◽  
Fei Wang ◽  
Richmond Lee ◽  
Yunbo Lv ◽  
Kuo-Wei Huang ◽  
...  
Keyword(s):  
Amino Acid ◽  
Dft Calculations ◽  
Diels Alder ◽  
Amino Acid Derivatives

An aza-Michael addition protocol to fluoroalkylated β-amino acid derivatives and enantiopure trifluoromethylated N-heterocycles

2014 ◽  
Vol 16 (10) ◽  
pp. 4530-4534 ◽  
Author(s):  
Xing Yang ◽  
Zhuo Chen ◽  
Yuan Cai ◽  
Yi-Yong Huang ◽  
Norio Shibata
Keyword(s):  
Amino Acid ◽  
Michael Addition ◽  
Solvent Free ◽  
Amino Acid Derivatives ◽  
Solvent Free Conditions

Aza-Michael addition under catalyst- and solvent-free conditions worked well to install various fluoroalkylated amino acid derivatives and three trifluoromethylated heterocycles.

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