Iridium-catalyzed asymmetric hydrogenation of <i>β</i>-keto esters with new phenethylamine-derived tridentate P,N,N-ligands

Wei, De-Quan; Chen, Xiu-Shuai; Hou, Chuan-Jin; Hu, Xiang‐Ping

doi:10.1080/00397911.2018.1550203

Cited by 8 publications

(2 citation statements)

References 19 publications

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“…However, dimerization of the catalyst was observed. In 2019, Hu 121 and co-workers developed a new PNN ligand PNN-L20 based on f-Amphox by replacing phosphanyl ferrocene with phosphanyl benzene. Planar chirality was lost in the new ligand.…”

Section: Pnn-type Ligandsmentioning

confidence: 99%

“…The in situ formed Ir catalyst gave 97.7% ee , 99% conversion, and 100,000 TON on ADH of acetophenone. In 2019, Hu and co-workers developed PNN-L19 based on f -amphox ( PNN-L10 ) by replacing the ferrocene moiety with benzene. Employing in situ formed Ir catalyst in ADH of β-keto-ester gave up to 82% ee and 98% conversion.…”

Section: Transition Metal-catalyzed Hydrogenation Reactions With Chir...mentioning

confidence: 99%

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Chiral Tridentate Ligands in Transition Metal-Catalyzed Asymmetric Hydrogenation

2021

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Asymmetric hydrogenation (AH) of double bonds has been one of the most effective methods for the preparation of chiral molecules and for the synthesis of important chiral building blocks. In the past 60 years, noble metals with bidentate ligands have shown marvelous reactivity and enantioselectivity in asymmetric hydrogenation of a series of prochiral substrates. In recent years, developing chiral tridentate ligands has played an increasingly important role in AH. With modular frameworks and a variety of functionalities on the side arms, chiral tridentate ligand complexes enable both reactivities and stereoselectivities. Although great achievements have been made for noble metal catalysts with chiral tridentate ligands since the 1990s, the design of chiral tridentate ligands for earth abundant metal catalysts has still been in high demand. This review summarizes the development of chiral tridentate ligands for homogeneous asymmetric hydrogenation. The philosophy of ligand design and the reaction mechanisms are highlighted and discussed as well.

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Section: Pnn-type Ligandsmentioning

confidence: 99%

Section: Transition Metal-catalyzed Hydrogenation Reactions With Chir...mentioning

confidence: 99%

Chiral Tridentate Ligands in Transition Metal-Catalyzed Asymmetric Hydrogenation

2021

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Chiral P,N,N‐Ligands for Asymmetric Hydrogenation

Liang,

Hou,

et al. 2024

Adv Synth Catal

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The chiral P,N,N‐ligands represented a new type of tridentate ligand developed in recent years and displayed wide utilities in asymmetric catalysis. In the past decades, numerous chiral P,N,N‐ligands with ferrocene, phenethylamine and spiro backbones were synthesized by addition of an aminopyridine, imidazole or diamines coordinating group. These chiral tridentate P,N,N‐ligands showed excellent performance in the ruthenium, iridium, manganese, or cobalt‐catalyzed asymmetric hydrogenations. A wide range of substrates, including simple ketones, α‐halogenated ketones, α‐hydroxy ketones, α‐ or β‐amino ketones, α‐, γ‐, or δ‐keto acids, α‐ or β‐keto amides, β‐ or δ‐keto esters, α‐ or β‐enones, olefins, imines, quinolines and indoles, could be hydrogenated to afford the corresponding chiral products with high yields and enantioselectivities. In this review, progress on the asymmetric hydrogenation of C=O, C=N, C=C bonds with chiral tridentate P,N,N‐ligands was summarized.

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