Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Wang, Yu-Heng; Hu, Pan; Wang, Xi-Rui; Xu, Ke-Lan; Wang, Qi-Lin; Wang, Hui-Juan; Liu, Xiong-Li

doi:10.1039/d3qo01748f

Org. Chem. Front.

2024

DOI: 10.1039/d3qo01748f

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Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Yu-Heng Wang,

Pan Hu,

Xi-Rui Wang

et al.

Abstract: A new class of chiral bipyridine-2NO ligands, which incorporate the advantages of both the bipyridine skeleton and the pyrroloimidazolone-based N-oxide moiety, was developed.

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Cited by 3 publications

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Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

Zhu,

Tian,

Liu

et al. 2024

Org. Lett.

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A novel type of highly efficient chiral C2-symmetric bipyridine-N,N′-dioxides ligand application in catalyzing Michael addition/Cyclization of 5-aminopyrazoles with α,β-unsaturated 2acyl imidazoles has been developed, affording the corresponding adducts in 85−97% yield with up to 99% enantioselectivity under mild conditions with a lower catalyst loading and broad scope. Remarkably, this protocol exhibits advantages in terms of reactivity and enantioselectivity, giving the fact that as low as 2.2 mol % of L1 and 2.0 mol % of Ni(OTf) 2 can promote the title reaction on gram scale to afford the desired product with excellent enantioselectivity.

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Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

Zhu,

Tian,

Liu

et al. 2024

Org. Lett.

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Phen-2NO, a new C₂-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles

Chen,

Xu,

Wang

et al. 2024

New J. Chem.

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Naphthyridine–2NO, a new C₂-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

Hu,

Xu,

Wang

et al. 2024

Org. Chem. Front.

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Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Abstract: A new class of chiral bipyridine-2NO ligands, which incorporate the advantages of both the bipyridine skeleton and the pyrroloimidazolone-based N-oxide moiety, was developed.

Cited by 3 publications

References 82 publications

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

Phen-2NO, a new C₂-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles

Naphthyridine–2NO, a new C₂-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

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Design of rigid chiral bipyridine-2NO tetradentate ligands: application in asymmetric catalysis

Abstract: A new class of chiral bipyridine-2NO ligands, which incorporate the advantages of both the bipyridine skeleton and the pyrroloimidazolone-based N-oxide moiety, was developed.

Cited by 3 publications

References 82 publications

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

Bipyridine-N,N′-dioxides Catalysts: Design, Synthesis, and Application in Asymmetric Synthesis of 1H-Pyrazolo[3,4-b]pyridine Analogues

Phen-2NO, a new C2-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles

Naphthyridine–2NO, a new C2-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation

Contact Info

Product

Resources

About

Phen-2NO, a new C₂-symmetric rigid-featured tetradentate ligand, and its application in the asymmetric alkylation reaction of indoles

Naphthyridine–2NO, a new C₂-symmetric rigid tetradentate bimetallic ligand and its application in asymmetric Friedel–Crafts alkylation