Sulfonated asphaltene as a highly efficient catalyst for the Mannich reaction with excellent diastereoselectivity and recyclability DOI Creative Commons
Navid Habibnejad, Najmedin Azizi, Mohsen Hajibeygi

et al.

Scientific Reports, Journal Year: 2024, Volume and Issue: 14(1)

Published: Dec. 28, 2024

This study investigates the repurposing of asphaltene, a petroleum waste product, as catalyst for organic reactions. Sulfonated asphaltene was synthesized and evaluated its efficacy in catalyzing Mannich reaction, displaying notable diastereoselectivity operating effectively under mild conditions. Characterization catalyst's chemical composition, structure, thermal stability conducted using FT-IR, TGA, XRD, CHN, BET-BJH, SEM, EDS analyses. Employing sulfonated one-pot multi-component reaction to generate β-amino carbonyl derivatives ethanol resulted high product yields after 4–7 h. Notably, exhibited recyclability, demonstrating reusability at least 10 cycles.

Language: Английский

Solvent‐Controlled Enantiodivergent Construction of P(V)‐Stereogenic Molecules via Palladium‐Catalyzed Annulation of Prochiral N‐Aryl Phosphonamides with Aromatic Iodides DOI

Qingyu Tian,

Jin Ge,

Yaopeng Liu

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(41)

Published: July 9, 2024

In this work, we describe an efficient and modular method for enantiodivergent accessing P(V)-stereogenic molecules by utilizing the catalytic atroposelective Catellani-type C-H arylation/desymmetric intramolecular N-arylation cascade reaction. The enantioselectivity of protocol was proved to be tuned polarity solvent, thus providing a wide range both chiral enantiomers in moderate good yields with excellent enantiomeric excesses. Noteworthy is that strategy developed herein represents unprecedented example solvent-dictated inversion compounds.

Language: Английский

Citations

4

Temperature‐Dependent Regiodivergent Synthesis of Functionalized Maleimides and Itaconimides via in‐situ Generated Pyridinium Ylide DOI Open Access
Suman Saha,

Anupriya Bera,

Akanksha Kumari

et al.

European Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 11, 2025

Abstract We report a temperature‐dependent regiodivergent synthetic strategy for the construction of functionalized maleimides and itaconimides using in‐situ generated pyridinium ylides. This approach enables efficient access to both regioisomeric products under mild straightforward reaction conditions. A variety salts with different aromatic alkyl groups were successfully used N ‐aryl ‐alkyl succinimides demonstrating broad substrate compatibility. The practicality scalability this methodology confirmed through scale‐up experiments, which maintained high yields reproducibility.

Language: Английский

Citations

0

Green Catalysis: Water as a Sustainable Medium in Organocatalyzed Reactions DOI

Arbia Fatima,

Anam Shahzadi,

Adnan Majeed

et al.

Langmuir, Journal Year: 2025, Volume and Issue: unknown

Published: March 22, 2025

The use of organocatalysts has increased significantly in recent years due to their tremendous applications green solvents. Thus, using water as a solvent evolved critical factor. Organocatalysts are efficient and sustainable agents for promoting chemical reactions water. literature been extensively reviewed, the various three fundamental C–C bond-forming processes─the Aldol, Michael, Mannich aqueous media─have compiled this study. can overcome limitations conventional organic solvents by achieving high reaction rates regioselectivity This Review highlights advantages media these key reactions. It discusses principles behind designing effective organocatalysts, focusing on impact selectivity, sustainability, efficiency. study also summarizes most significant advancements over past decade.

Language: Английский

Citations

0

(S)-Convergent Deracemization of Racemic Esters with (R)-Selective Lipase: Pickering Emulsion Strategy for Enantiodivergent Synthesis Using a Native Enzyme DOI

Tomoya Nishio,

Shuji Akai, Kyohei Kanomata

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 6565 - 6571

Published: April 7, 2025

Language: Английский

Citations

0

A stereodivergent multicomponent approach for the synthesis of C–N atropisomeric peptide analogues DOI Creative Commons

Natalie J. Roper,

Aaron D. G. Campbell, Paul G. Waddell

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Four-component reactions at room temperature delivered C–N atropisomeric peptide analogues possessing both central and axial chirality with complete diastereocontrol. Reactions elevated selectively afforded the other diastereoisomer.

Language: Английский

Citations

3

Solvent‐Controlled Enantiodivergent Construction of P(V)‐Stereogenic Molecules via Palladium‐Catalyzed Annulation of Prochiral N‐Aryl Phosphonamides with Aromatic Iodides DOI

Qingyu Tian,

Jin Ge,

Yaopeng Liu

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(41)

Published: July 9, 2024

Abstract In this work, we describe an efficient and modular method for enantiodivergent accessing P(V)‐stereogenic molecules by utilizing the catalytic atroposelective Catellani‐type C−H arylation/desymmetric intramolecular N ‐arylation cascade reaction. The enantioselectivity of protocol was proved to be tuned polarity solvent, thus providing a wide range both chiral enantiomers in moderate good yields with excellent enantiomeric excesses. Noteworthy is that strategy developed herein represents unprecedented example solvent‐dictated inversion compounds.

Language: Английский

Citations

1

Solvent-Controlled Diastereodivergent Synthesis of Hexahydropyrrolo[2,1-a]isoquinolines through Pd/C-Catalyzed Dehydrogenative [3 + 2] Cycloaddition DOI

Ji-Chao Lu,

Hao Bai,

Ying Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 10, 2024

A Pd/C-catalyzed dehydrogenative [3 + 2] cycloaddition is described for the diastereoswitchable synthesis of hexahydropyrrolo[2,1-a]isoquinolines by altering solvents. The reaction proceeds through a sequential formation azomethine ylides from tetrahydroisoquinoline acetates and 1,3-dipolar with 2-nitroethenylbenzenes. This method displayed tunable diastereoselectivity, broad substrate scope good functional group compatibility. Moreover, gram-scale selective reductive or oxidative transformations product further demonstrate utility this methodology.

Language: Английский

Citations

1

Trifluoroethanol Promoted Formal Nucleophilic Substitution of Indol-2-yl Diaryl Methanol for the Synthesis of Tetraarylmethanes DOI

Cuicui Nian,

Runsheng Yu, Zhengyu Han

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(72), P. 9797 - 9800

Published: Jan. 1, 2024

The synthesis of tetraarylmethanes has long been a challenge in the field synthetic chemistry. In this study, series were successfully synthesized through formal nucleophilic substitution reaction indol-2-yl diaryl methanol catalyzed by Brønsted acid. key success study lies suppressing influence water molecules forming hydrogen bonds with TFE solvent. This process leads to formation active 2-indole imine methide (2-IIM) intermediates, ensuring successful tetraarylmethanes. Furthermore, some products also exhibited potential anticancer activity.

Language: Английский

Citations

0

Tungsten-Catalyzed Stereodivergent Isomerization of Terminal Olefins DOI Creative Commons
Tanner C. Jankins, Camille Rubel, Hang Chi Ho

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 4, 2024

A stereodivergent, W-catalyzed alkene isomerization is reported, leading to either E - or Z -β,γ-unsaturated carbonyl compounds based on the ligand environment around metal.

Language: Английский

Citations

0

Diastereodivergence in catalytic asymmetric conjugate addition of carbon nucleophiles DOI
Byungjun Kim,

Hooseung Lee,

In‐Sun Song

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 11, 2024

Catalytic asymmetric conjugate additions of carbon nucleophiles have emerged as a potent tool for constructing multi-stereogenic molecules with precise stereochemical control. This review explores the concept diastereodivergence in such reactions, focusing on strategies to achieve selective access diverse diastereomeric products upon carbon-carbon bond formation. Drawing from rich array examples, we delve into key approaches controlling outcome these transformations, including alteration alkene geometry, fine-tuning reaction parameters, synergistic catalysis, and isomerization adducts. Additionally, highlight iterative additions, showcasing their potential diastereodivergent synthesis methyl-branched stereocenters 1,3-relationships. By presenting concentrated overview this significant topic, aims provide valuable insights design execution stereodivergent catalytic offering new avenues advancing stereoselective structural diversity organic synthesis.

Language: Английский

Citations

0