Pd(II) Complexes of Chiral Proline-Derived Ligands: Application for Dynamic Thermodynamic Resolution of α-Amino Acids and Their Antibacterial Activities

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3808 - 3821

Published: March 3, 2023

Novel type of Pd(II) complexes have been synthesized under operationally simple and convenient conditions applied in the dynamic thermodynamic resolution racemic N,C-unprotected α-amino acids. After rapid hydrolysis, these produced corresponding acids satisfactory yields enantioselectivities, accompanied by recyclable proline-derived ligand. In addition, method can be readily for S/R interconversion to obtain unnatural (R)-α-amino from available (S)-α-amino Furthermore, biological assays showed that (S,S)-3i (S,S)-3m exhibited significant antibacterial activities similar vancomycin, which may represent promising lead structures further development agents.

Language: Английский

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Revolutionizing C–H Activation Reactions: Harnessing Green Solvents for Sustainable Catalysis

Synthesis, Journal Year: 2024, Volume and Issue: 56(15), P. 2329 - 2338

Published: Jan. 10, 2024

Abstract This short review showcases the developing field of C–H activation reactions, with a particular focus on green catalysis through use environmentally friendly solvents. It evaluates effects these solvents reaction outcomes, environmental aspects and general efficacy, highlighting their advantages that lead to greater selectivity, lower levels toxicity enhanced rates. Water biobased alternatives such as polyethylene glycols, glycerol, 2-methyltetrahydrofuran, γ-valerolactone, methanol, ethanol, p-cymene diethyl carbonate are representative examples The scope this encompasses studies different methodologies, catalysts, conditions help develop reactions utilizing 1 Introduction 2 3 Polyethylene Glycols (PEGs) 4 Glycerol 5 2-Methyltetrahydrofuran (2-MeTHF) 6 γ-Valerolactone (GVL) 7 Methanol 8 Ethanol 9 p-Cymene 10 Diethyl Carbonate 11 Conclusion

Language: Английский

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A Stereoselective Entry to Enantiopure (S)-2-Amino-2-methyl-5-arylpent-4-ynoic Acids and Evaluation of Their Inhibitory Activity against Bacterial Collagenase G

Symmetry, Journal Year: 2023, Volume and Issue: 15(10), P. 1924 - 1924

Published: Oct. 16, 2023

Nowadays, amino acids (AAs) and peptides with bulky side chains hold significant interest for organic synthesis the modern pharma industry. Non-proteinogenic (or unnatural) AAs are key building blocks used obtaining pharmaceutically relevant development of chiral molecular catalysts, they extensively in total complex natural compounds. Thus, an elaboration cost-effective methods preparation novel unnatural to increase their structural diversity is highly desirable. In this context, herein, we present asymmetric metal-templated a number enantiomerically pure (S)-2-amino-2-methyl-5-arylpent-4-ynoic starting from commercially available reagents Belokon’s auxiliary (S)-BPB, namely (S)-2-(N-benzylprolyl)aminobenzophenone. The construction Ni(II) alanine (Ala) subsequent propargylation, arylation by Sonogashira cross-coupling reaction using various aryl halides, and, finally, acidic decomposition obtained complexes deliver target α,α-disubstituted featuring triple bond chain. Next, Fmoc-protected α-AAs dipeptide were synthesized. Finally, examined peptide as collagenase inhibitors.

Language: Английский

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A synthetic route to artificial chiral α-amino acids featuring a 3,4-dihydroisoquinolone core through a Rh(iii)-catalyzed functionalization of allyl groups in chiral Ni(ii) complexes

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9143 - 9149

Published: Jan. 1, 2023

The first asymmetric synthetic route to artificial α-amino acids with a 3,4-dihydroisoquinolone skeleton was elaborated via straightforward Rh( iii )-catalyzed C–H activation/annulation reaction.

Language: Английский

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