RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones <i>via</i> a dynamic kinetic resolution

Li, Jingjing; Ye, Jianxun; Zhou, Jiayu; Li, Jing; Liu, Delong; Zhang, Wanbin

doi:10.1039/d2cc01193j

Cited by 10 publications

(4 citation statements)

References 46 publications

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“…To further rule out a possible transfer hydrogenation process, the reaction was carried out under the optimal reaction conditions in the absence of H 2 , but failed (Scheme 6, middle). Considering our previous work, [10j] it is believed that a hydrogen‐deuterium exchange rather than a transfer hydrogenation process might occur during the reaction (Scheme 6, bottom).…”

Section: Methodsmentioning

confidence: 89%

Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

Zhou

Zhang

et al. 2023

Adv Synth Catal

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The RuPHOX‐Ru catalyzed asymmetric hydrogenation of diaryl ketones has been established, providing the corresponding chiral diaryl methanols in up to 99% yield and 99% ee. The protocol could be performed on a gram‐scale with a relatively low catalyst loading (2000 S/C) and the resulting products allow for several useful transformations, in particular for the synthesis of chiral drugs, such as, (S)‐Orphenadrine and (S)‐Neobenodine. Deuterium labeling and control experiments revealed that the RuPHOX‐Ru‐catalyzed asymmetric hydrogenation is fully subject to hydrogenation with H2 as the sole hydrogen source.

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Section: Methodsmentioning

confidence: 89%

Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

Zhou

Zhang

et al. 2023

Adv Synth Catal

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“…[ 13 ] Our group has previously developed the planar chiral RuPHOX‐Ru catalyst which has been successfully applied to asymmetric hydrogenations of substrates bearing C═C and/or C═O double bonds. [ 14 ] In this context, the reduction of the aforementioned double bonds can be achieved under mild reaction conditions by using bases with different alkalinity. We therefore applied this chiral ( S , S p )‐Ru‐catalyst to the asymmetric hydrogenation of 1a with the aim of achieving the chemo‐ and enantioselective hydrogenation of the two types of double bonds ( Table 1 ).…”

Section: Resultsmentioning

confidence: 99%

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

He,

Li,

et al. 2024

Advanced Science

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

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“…In 2022, there will be exceptional enantioselectivities and diastereoselectivities (up to 99.9% ee and 420:1 dr) (Scheme 28). 79,80 The solvents EtOH and t BuOH were employed, and milder conditions such as room temperature and 2-h reaction time were the main advantages of this work.…”

Section: Ru Catalyzed Synthesismentioning

confidence: 99%

A concise review on recent advances in catalytic asymmetric hydrogenation

et al. 2023

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Accounts on the recent (over the past 10 years) catalytic asymmetric hydrogenation reaction‐based achievements with different catalysts to generate natural products and synthetic targets such as fragrances, pharmaceutical agents, and agrochemicals are mentioned in this present concise review. Mechanistic steps, chemoselectivity with higher functional group tolerance by employing transition metal‐based chiral catalysts (Ir‐, Rh‐, Ni‐, Ru‐, Fe‐, Mn‐, Pd‐, Co‐, and Zn‐based organometallic chiral complexes), and biocatalysts and their importance on the genesis of chirality coupled with higher turnover numbers are also described.

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RuPHOX–Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution

Abstract: The efficient RuPHOX-Ru catalyzed asymmetric hydrogenation of α-substituted tetralones via a dynamic kinetic resolution has been achieved for the synthesis of chiral tetrahydronaphthols. The mechanism study indicated that the hydrogenation...

Cited by 10 publications

References 46 publications

Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

Synthesis of Chiral Diaryl Methanols via RuPHOX‐Ru Catalyzed Asymmetric Hydrogenation

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

A concise review on recent advances in catalytic asymmetric hydrogenation

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