Random Forest‐Based Prediction of Enantioselectivity in Thiol Addition to Imines Catalyzed by Chiral Phosphoric Acids DOI
Xinliang Yu, Zekai Zhang

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(40)

Published: Oct. 1, 2024

Abstract This paper, for the first time, reports calculating molecular descripts from combinations of catalysts and substrates, enantioselectivity predictions in chiral phosphoric acid–catalyzed thiol addition to N ‐acylimines. Ten descriptors, together with random forest (RF) algorithm, were used establish quantitative structure–selectivity relationship (QSSR) model (RF Model I), yielding correlation coefficient R =0.982, root mean square ( rms ) error 0.604 kJ/mol (for 800 ΔΔG 32 training set), =0.922, =1.075 275 11 new test set). The RF I was proved be more accurate predictions, compared QSSR models reported literature II III this work. Moreover, based on simple Dragon descriptors capable extrapolative prediction catalysts. Therefore, it is reasonable deriving substrates (thiols imines). work provides a method .

Language: Английский

Unlocking the Phosphoric Acid Catalyzed Asymmetric Transfer Hydrogenation of 2-Alkenyl Quinolines for Efficient Flow Synthesis of Hancock Alkaloids DOI Creative Commons
Bence S. Nagy, Aitor Maestro, Miquel À. Pericàs

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 21, 2025

Chiral tetrahydroquinolines are present in several bioactive molecules, such as the Hancock alkaloids. Although organocatalytic asymmetric transfer hydrogenation of 2-aryl quinolines has emerged a safer alternative to using hydrogen gas, analogous reactions with 2-alkenyl remain unexplored. Here we protocol synthesize key enantioenriched intermediates alkaloids, providing constant outcome for, at least, 24 h continuous flow operation.

Language: Английский

Citations

0
De novo construction of amine-functionalized metal-organic cages as heterogenous catalysts for microflow catalysis DOI Creative Commons
Yingguo Li,

Jialun He,

Guilong Lu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Aug. 15, 2024

Microflow catalysis is a cutting-edge approach to advancing chemical synthesis and manufacturing, but the challenge lies in developing efficient stable multiphase catalysts. Here we showcase incorporating amine-containing metal-organic cages into automated microfluidic reactors through covalent bonds, enabling highly continuous flow catalysis. Two Fe4L4 tetrahedral bearing four uncoordinated amines were designed synthesized. Post-synthetic modifications of amine groups with 3-isocyanatopropyltriethoxysilane, introducing silane chains immobilized on inner walls reactor. The prove for reaction anthranilamide aldehydes, showing superior reactivity recyclability relative free cages. This superiority arises from large cavity, facilitating substrate accommodation conversion, high mass transfer rate bonds between cage microreactor. study exemplifies synergy microreactor technology, highlighting benefits heterogenous potential future processes represents method though catalysts remains challenging. authors demonstrate incorporation

Language: Английский

Citations

2
General and Versatile Synthesis of Highly Recyclable Chiral Phosphoric Acid Organocatalysts DOI Creative Commons
Aitor Maestro, Sándor B. Ötvös, Gerald Auer

et al.

Published: July 29, 2024

The development of recyclable catalysts has gained more attention in recent years order to minimize the environmental effect and overall cost catalytic processes. Some most broadly used chiral organocatalysts are BINOL-derived phosphoric acids, making it necessary develop efficient recycling strategies. While literature reports require up 13 synthetic steps access here we report a general concise 9-step approach anthracene decorated heterogeneous acids (PS-Anth), which have shown high performance either batch or continuous flow without observing catalyst degradation.

Language: Английский

Citations

1
Enhanced Recyclability of Polymer Brush-Supported Sulfonic Acid with Diblock Architecture DOI

Jingjing Zhao,

Zhe Cui, Shiyi Zhang

et al.

ACS Applied Polymer Materials, Journal Year: 2024, Volume and Issue: 6(17), P. 10977 - 10985

Published: Aug. 27, 2024

Solid polymer brush-supported molecular catalysts generally exhibit activity comparable to catalysts, but they suffer the problems of decreased with increasing recycled times in reactions. This study explores use brushes a diblock architecture design durable silica-based sulfonic acid catalysts. Two brush materials, differing amounts polystyrene (PS) brush, were prepared by first growing PS using copper-catalyzed ARGET SI-ATRP and poly(vinylimidazole) SI-ATRP. The resulting then reacted 1,3-propane sultone trifluoromethanesulfonic obtain two solid For comparison, without layer was also prepared. These acidic applied synthesize acylals from aldehydes acetic anhydride. acids demonstrated superior compared catalyst. Notably, catalyst protection could be 15 (yield ≥95%) decrease activity; contrast, yield 35% 10th run. Thermogravimetric analysis indicated 3% loss materials for 9.5% layer, after specified numbers runs. Polymer probably finds more applications solid-based

Language: Английский

Citations

1
General and versatile synthesis of highly recyclable chiral phosphoric acid organocatalysts DOI
Aitor Maestro, Sándor B. Ötvös, Gerald Auer

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(20), P. 5901 - 5907

Published: Jan. 1, 2024

The development of recyclable catalysts has gained more attention in recent years order to minimize the environmental effect and overall cost catalytic processes. Some most broadly used chiral organocatalysts are BINOL-derived phosphoric acids, making it necessary develop efficient recycling strategies. While literature reports require up 13 synthetic steps access here we report a general concise 9-step approach anthracene decorated heterogeneous acids (PS-Anth), which have shown high performance either batch or continuous flow without observing catalyst degradation.

Language: Английский

Citations

1
Random Forest‐Based Prediction of Enantioselectivity in Thiol Addition to Imines Catalyzed by Chiral Phosphoric Acids DOI
Xinliang Yu, Zekai Zhang

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(40)

Published: Oct. 1, 2024

Abstract This paper, for the first time, reports calculating molecular descripts from combinations of catalysts and substrates, enantioselectivity predictions in chiral phosphoric acid–catalyzed thiol addition to N ‐acylimines. Ten descriptors, together with random forest (RF) algorithm, were used establish quantitative structure–selectivity relationship (QSSR) model (RF Model I), yielding correlation coefficient R =0.982, root mean square ( rms ) error 0.604 kJ/mol (for 800 ΔΔG 32 training set), =0.922, =1.075 275 11 new test set). The RF I was proved be more accurate predictions, compared QSSR models reported literature II III this work. Moreover, based on simple Dragon descriptors capable extrapolative prediction catalysts. Therefore, it is reasonable deriving substrates (thiols imines). work provides a method .

Language: Английский

Citations

0