Copper-Catalyzed Intermolecular [2 + 2 + 2] Annulation of Diynes with Alkynes: Construction of Carbazoles

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

Transition-metal-catalyzed [2 + 2 2] annulation of alkynes is an efficient pathway for the synthesis aromatic compounds. However, most established methods require noble metal catalysts. Herein, we report a copper-catalyzed intermolecular diynes with through vinyl cation intermediates, enabling atom-economical preparation biologically important carbazole skeletons. The reaction shows good regioselectivity in aryl(alkyl)alkynes. Moreover, preliminary results have also been obtained related catalytic atroposelective transformation. This represents rare example non-noble-metal-catalyzed ynamides pathway.

Язык: Английский

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Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(10), С. 2857 - 2863

Опубликована: Янв. 1, 2024

A Rh-catalyzed neighboring group-directed asymmetric [2 + 2 2] cycloaddition of 1,6-diynes and ynamides to generate C–N axially chiral indole derivatives has been developed.

Язык: Английский

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Enantioselective [2+2+2] Cycloaddition of Internal Alkynes to Access Axially Chiral Biaryl Hexasubstituted Benzene

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 2939 - 2949

Опубликована: Фев. 4, 2025

Язык: Английский

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Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle

Molecules, Год журнала: 2024, Номер 29(14), С. 3363 - 3363

Опубликована: Июль 17, 2024

A novel axially chiral all-hydrocarbon cyclo[7] (1,3-(4,6-dimethyl)benzene (

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Rhodium-Catalyzed Regioselective [4 + 2] Cycloaddition of Ynamines and 2-(Cyanomethyl)phenylboronates

Organic Letters, Год журнала: 2024, Номер 26(31), С. 6586 - 6590

Опубликована: Июль 30, 2024

A rhodium-catalyzed [4 + 2] cycloaddition of ynamines and 2-(cyanomethyl)phenylboronates has been developed, leading to efficient excellent regioselective synthesis valuable indole-linked aromatic compounds in a concise flexible approach. Interestingly, this strategy was successful the construction C···N axially chiral indoles with high enantiocontrol by introduction new phosphoramidite ligand (Xie-Phos).

Язык: Английский

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Asymmetric Rh‐Catalyzed [2+2+2] Cycloaddition: Synthesis of N‐Alkenylindoles with both Axial and Central Chirality

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Сен. 3, 2024

Abstract Axially chiral indoline‐based scaffolds are virtually universal in biological and pharmaceutical compounds. In this study, we demonstrate the Rh‐catalyzed asymmetric [2 + 2 2] cycloaddition of 1,6‐enynes with steric hindered N‐ alkynyl indoles, which enables simultaneous construction both axial central chirality, containing a quaternary carbon center, one step. Notable features these reactions include excellent chemo‐, regio‐, diastereo‐ enantioselectivity, 100% atom‐economy, easily available SEGPHOS ligand, mild conditions.

Язык: Английский

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Stereodivergent Synthesis of Atropisomeric Indole-Fused δ-Lactams Bearing All-Carbon Quaternary Stereocenters via Cu-Catalyzed Desymmetric Arene Amidation

ACS Catalysis, Год журнала: 2024, Номер unknown, С. 16639 - 16648

Опубликована: Окт. 28, 2024

Язык: Английский

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Gold/HNTf₂-Cocatalyzed Asymmetric Annulation of Diazo-Alkynes: Divergent Construction of Atropisomeric Biaryls and Arylquinones

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 30, 2024

Due to the inherent challenges posed by linear coordination of gold(I) complexes, asymmetric gold-catalyzed processes remain challenging, particularly in atroposelective synthesis axially chiral skeletons. Except for extremely few examples intramolecular annulations, construction axial chirality via intermolecular alkyne transformation is still undeveloped. Herein, a gold/HNTf

Язык: Английский

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