The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13235 - 13242
Published: Sept. 10, 2024
This study presents the synthesis of novel naphthofurano-iminosugars (
Language: Английский
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(3), P. 1475 - 1496
Published: Jan. 16, 2023
Multicomponent reactions (MCRs) combine at least three reactants to afford the desired product in a highly atom-economic way and are therefore viewed as efficient one-pot combinatorial synthesis tools allowing one significantly boost molecular complexity diversity. Nowadays, MCRs no longer confined organic have found applications materials chemistry. In particular, can be used prepare covalent frameworks (COFs), which crystalline porous assembled from monomers exhibit broad range of properties applications. This synthetic approach retains advantages small-molecule MCRs, not only strengthening skeletal robustness COFs, but also providing additional driving forces for their crystallization, has been series robust COFs with diverse The present perspective article provides general background discusses types employed COF date, addresses related critical challenges future perspectives inspire MCR-based design new promote further progress this emerging field.
Language: Английский
Citations
112
Pharmaceuticals, Journal Year: 2022, Volume and Issue: 15(8), P. 1009 - 1009
Published: Aug. 17, 2022
Multicomponent reactions 9i.e., those that engage three or more starting materials to form a product contains significant fragments of all them), have been widely employed in the construction compound libraries, especially context diversity-oriented synthesis. While relatively less exploited, their use target-oriented synthesis offers advantages terms synthetic efficiency. This review provides critical summary multicomponent for preparation active pharmaceutical principles.
Language: Английский
Citations
42
Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(17), P. 3477 - 3502
Published: Jan. 1, 2023
This review article presents an in-depth analysis of the strategies and methodologies for using chiral phosphoric acids as organocatalysts in asymmetric syntheses from recent literature.
Language: Английский
Citations
32
Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)
Published: June 8, 2023
Heterohelicenes are of increasing importance in the fields materials science, molecular recognition, and asymmetric catalysis. However, enantioselective construction these molecules, especially by organocatalytic methods, is challenging, few methods available. In this study, we synthesize enantioenriched 1-(3-indol)-quino[n]helicenes through chiral phosphoric acid-catalyzed Povarov reaction followed oxidative aromatization. The method has a broad substrate scope offers rapid access to an array quinohelicenes with enantioselectivities up 99%. Additionally, photochemical electrochemical properties selected explored.
Language: Английский
Citations
32
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: June 7, 2024
Inherently chiral calix[4]arenes are an excellent structural scaffold for enantioselective synthesis, recognition, sensing, and circularly polarized luminescence. However, their catalytic synthesis remains challenging. Herein, we report efficient of inherently calix[4]arene derivatives via cascade cyclization oxidation reactions. The three-component reaction features a broad substrate scope (33 examples), high efficiency (up to 90 % yield), enantioselectivity (>95 ee on average). potential applications highlighted by synthetic transformation detailed investigation photophysical chiroptical properties.
Language: Английский
Citations
10
Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 22, 2025
The synthesis of chiral tetrahydroquinolines (THQs) has garnered significant interest from medicinal chemists due to their frequent presence as pharmacophores in bioactive compounds. While existing synthetic methods have primarily focused on THQs with single or multiple endocyclic centers, the selective construction both endo- and exo-cyclic centers remains a challenge that requires further development. This study introduces dynamic kinetic resolution (DKR)-based transfer hydrogenation racemic 2-substituted quinolines, which yields structurally novel consecutive excellent stereoselectivities (59 examples, generally >20:1 dr >90% ee, up three stereocenters). Our approach offers mechanistically method for asymmetric transformation electron-deficient aromatic N-heterocycles presents an innovative way expand N-heterocycle chemical space chemistry.
Language: Английский
Citations
1
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)
Published: July 8, 2024
Inherently chiral calix[4]arenes represent a unique type of molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the inherently through sequential organocatalyzed Povarov reaction and aromatizations. The phosphoric acid catalyzed three-component involving amino group-substituted calix[4]arenes, aldehydes (di)enamides desymmetrized prochiral calix[4]arene substrates, which was followed by various aromatization methods, resulting in diverse array novel quinoline-containing good yields high enantioselectivities (up to 75 % yield, 99 ee). large-scale derivatizations products highlight value this method. Furthermore, preliminary exploration into photophysical chiroptical properties demonstrate potential applications these molecules.
Language: Английский
Citations
7
Topics in Current Chemistry, Journal Year: 2023, Volume and Issue: 381(4)
Published: May 30, 2023
Abstract Nitrogen heterocycles are part of the structure natural products and agents with important biological activity, such as antiviral, antibiotic, antitumor drugs. For this reason, heterocyclic compounds one today’s most desirable synthetic targets Povarov reaction is a powerful tool for construction highly functionalized systems. This process involves an aromatic amine, carbonyl compound, olefin or acetylene to give rise formation nitrogen-containing heterocycle. review illustrates advances in aspects intramolecular intricate polyheterocyclic compounds. original presents research done field, references works by internationally relevant groups on current topic, covering literature from 1992 2022. The reactions described here according key processes involved, using different combinations heteroaromatic amines, aliphatic, aromatic, aldehydes. Some catalytic promoted transition metals detailed, well oxidative some asymmetric processes.
Language: Английский
Citations
13
Synthesis, Journal Year: 2022, Volume and Issue: 54(14), P. 3162 - 3179
Published: March 10, 2022
Abstract The multicomponent Povarov reaction represents a powerful approach for the construction of substances containing N-heterocyclic frameworks. By using reaction, in addition to accessing tetrahydroquinolines, quinolines and julolidines single step, it is possible form following new bonds: two Csp 3–Csp 3 one 3–Nsp 3, 2–Csp 2 2–Nsp 2, four 1, respectively. This short review discusses main features including its mechanism, scope by employing different catalysts substrates, as well stereoselective versions. 1 Introduction Mechanism Reaction Tetrahydroquinolines 4 Quinolines 5 Julolidines 6 Concluding Remarks
Language: Английский
Citations
20
Advances in heterocyclic chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
Language: Английский
Citations
0