Bimetallic Ru/Ru‐Catalyzed Asymmetric One‐Pot Sequential Hydrogenations for the Stereodivergent Synthesis of Chiral Lactones

Advanced Science, Год журнала: 2024, Номер 11(23)

Опубликована: Март 21, 2024

Abstract Asymmetric sequential hydrogenations of α ‐methylene γ ‐ or δ ‐keto carboxylic acids are established in one‐pot using a bimetallic Ru/Ru catalyst system, achieving the stereodivergent synthesis all four stereoisomers both chiral and ‐lactones with two non‐vicinal carbon stereocenters high yields (up to 99%) excellent stereoselectivities >99% ee >20:1 dr). The compatibility Ru systems is investigated detail, it found that basicity reaction system plays key role hydrogenation processes. protocol can be performed on gram‐scale low loading 11000 S/C) resulting products allow for many transformations, particularly several intermediates useful preparation drugs natural products.

Язык: Английский

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Ru-Catalyzed Asymmetric Hydrogenation of α,β-Unsaturated γ-Lactams

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(36), С. 25312 - 25320

Опубликована: Сен. 2, 2024

A highly efficient Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated γ-lactams has been developed by using a

Язык: Английский

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Effect of Solvents on Electrogenerated Base-Driven Transfer Hydrogenation Reactions

Molecules, Год журнала: 2025, Номер 30(4), С. 910 - 910

Опубликована: Фев. 15, 2025

Transfer hydrogenation is a crucial technology for synthesizing fine chemicals and pharmaceuticals, offering improved safety convenience over traditional hydrogen methods, although it typically requires external bases. While isopropanol commonly used as source, methanol superior but faces challenges due to its high dehydrogenation energy barrier, limiting use under mild conditions. This study focuses on investigating the differences in electrogenerated base-driven transfer of aromatic ketones solvents, using Mn(CO)₅Br cyclohexanediamine derivatives catalyst. The research demonstrates that enantiomeric excess (ee) values were obtained presence chiral Mn-based catalysts, while only racemic products observed methanol. results indicate strong dependence catalytic pathway choice solvent: isopropanol, catalyst operates via metal-ligand cooperative hydrogenation, resulting ee values, whereas methanol, occurs through metal hydride with no stereoselectivity.

Язык: Английский

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Iridium-Catalyzed Asymmetric Hydrogenation of Aryl(4-hydroxyphenyl)ketones

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Май 28, 2025

Asymmetric hydrogenation of diaryl ketones is challenging, particularly when the two aromatic rings have very similar steric hindrances, such as those in para-substituted ketones. In this study, we developed a catalyst that can distinguish between para-hydroxyl phenyl and other aryl Using catalyst, variety chiral diarylcarbinols were synthesized with high yield enantioselectivity. DFT studies revealed noncovalent interactions π-π stacking C-H···π substrate play crucial role controlling stereochemistry.

Язык: Английский

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RuPHOX-Ru catalyzed asymmetric Guerbet reaction of secondary alcohols with primary alcohols

Tetrahedron, Год журнала: 2023, Номер 143, С. 133543 - 133543

Опубликована: Июль 11, 2023

Язык: Английский

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Manganese catalyzed asymmetric transfer hydrogenation of hindered ketones bearing a 2,6-disubstituted phenyl group

Journal of Catalysis, Год журнала: 2024, Номер 438, С. 115680 - 115680

Опубликована: Июль 31, 2024

Язык: Английский

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RuPHOX‐Ru Catalyzed Asymmetric Cascade Hydrogenation of 3‐Substituted Chromones for the Synthesis of Corresponding Chiral Chromanols

Chemistry - A European Journal, Год журнала: 2024, Номер 30(37)

Опубликована: Май 2, 2024

Abstract An efficient RuPHOX−Ru catalyzed asymmetric cascade hydrogenation of 3‐substituted chromones has been achieved under mild reaction conditions, affording the corresponding chiral chromanols in high yields with excellent enantio‐ and diastereoselectivities (up to 99 % yield, >99 ee >20 : 1 dr). Control reactions deuterium labelling experiments revealed that a dynamic kinetic resolution process occurs during subsequent C=O double bond, which is responsible for performance hydrogenation. The resulting products allow several transformations it was shown protocol provides practical alternative strategy synthesis their derivatives.

Язык: Английский

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Reduction of C O to CHOH by Metal-Catalyzed Hydrogenation and Transfer Hydrogenation

Elsevier eBooks, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Язык: Английский

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