Manganese-catalyzed asymmetric transfer hydrogenation of quinolines in water using ammonia borane as a hydrogen source

Mao, Wenhao; Song, Dingguo; Guo, Jiyuan; Zhang, Kali; Zheng, Changdi; Lin, Jie; Huang, Lian; Zheng, Lizhou; Zhong, Weihui; Ling, Fei

doi:10.1039/d4gc00506f

Green Chem.

2024

DOI: 10.1039/d4gc00506f

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Manganese-catalyzed asymmetric transfer hydrogenation of quinolines in water using ammonia borane as a hydrogen source

Wenhao Mao,

Dingguo Song,

Jiyuan Guo

et al.

Abstract: The first example of manganese-catalyzed asymmetric transfer hydrogenation of N-heteroaromatics in water is reported. This ATH reaction proceeds smoothly without the need for inert atmosphere protection in the presence of...

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Cited by 3 publications

References 66 publications

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A detailed DFT theoretical investigation of the mechanism of quinoline hydrogenation catalyzed by a (1,5-cyclooctadiene)rhodium(I) complex

Rosales,

Arrieta,

Baricelli

et al. 2025

Catalysis Today

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A detailed DFT theoretical investigation of the mechanism of quinoline hydrogenation catalyzed by a (1,5-cyclooctadiene)rhodium(I) complex

Rosales,

Arrieta,

Baricelli

et al. 2025

Catalysis Today

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Asymmetric Transfer Hydrogenation of Ketones Improved by PNN–Manganese Complexes

Su,

Ma,

Wang

et al. 2024

J. Org. Chem.

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Chiral manganese(I) complexes that contain carbocyclic-fused 8-amino-5,6,7,8-tetrahydroquinolinyl groups that are appended with distinct para-R substituents have proven to be effective catalysts in the asymmetric transfer hydrogenation (ATH) of a wide range of ketones (48 examples). Notably, Mn2 proved to be the most productive catalyst, allowing an outstanding turnover number of 8300 with catalyst loadings as low as 0.01 mol %. Furthermore, this catalytic protocol shows considerable promise for applications in the synthesis of chiral drugs such as Lusutrombopag.

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Manganese-Catalyzed Asymmetric Hydrogenation for Atroposelective Dynamic Kinetic Resolution of Heterobiaryl Ketone N-Oxides

Wan,

2024

ACS Catal.

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An atroposelective dynamic kinetic resolution of configurationally labile heterobiaryl ketone N-oxides via Mncatalyzed asymmetric hydrogenation has been disclosed. By use of a structurally finely tuned chiral ferrocenyl P,N,N-ligand, the hydrogenation proceeds smoothly under mild conditions with simultaneous installation of central and axial chirality, giving a wide range of atropisomeric 1-arylisoquinoline and 2-arylpyridine N-oxides bearing a chiral alcohol structure with high diastereo-and enantioselectivities. The diastereomer of the hydrogenation product could be readily prepared in a stereospecific way with the complete inversion of the central chirality via Mitsunobu reaction. The value of this central-and axial-chiral heterobiaryl N-oxide scaffold is preliminarily demonstrated by its successful utility as a chiral catalyst in asymmetric allylation of benzaldehyde with allyltrichlorosilane.

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Manganese-catalyzed asymmetric transfer hydrogenation of quinolines in water using ammonia borane as a hydrogen source

Abstract: The first example of manganese-catalyzed asymmetric transfer hydrogenation of N-heteroaromatics in water is reported. This ATH reaction proceeds smoothly without the need for inert atmosphere protection in the presence of...

Cited by 3 publications

References 66 publications

A detailed DFT theoretical investigation of the mechanism of quinoline hydrogenation catalyzed by a (1,5-cyclooctadiene)rhodium(I) complex

A detailed DFT theoretical investigation of the mechanism of quinoline hydrogenation catalyzed by a (1,5-cyclooctadiene)rhodium(I) complex

Asymmetric Transfer Hydrogenation of Ketones Improved by PNN–Manganese Complexes

Manganese-Catalyzed Asymmetric Hydrogenation for Atroposelective Dynamic Kinetic Resolution of Heterobiaryl Ketone N-Oxides

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