Enantioselective synthesis of chiral N-arylpyrroles through photoinduced desymmetrization

Green Synthesis and Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Март 1, 2025

Язык: Английский

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Enantioselective Desymmetrization of Biaryls via Cooperative Photoredox/Brønsted Acid Catalysis and Its Application to the Total Synthesis of Ancistrobrevolines

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 5, 2025

Photoredox catalysis has emerged as a powerful tool for forming and breaking chemical bonds, further taking hold with its integration asymmetric catalysis. While the dual-catalytic approach led to successful examples of control stereogenic centers, axes remained underexplored. In this study, an acylimine intermediate was generated through photoredox catalysis, symmetric substrate, 2-arylresorcinol, desymmetrized aid chiral phosphoric acid Using approach, center axis were successfully controlled provide natural-product-driven compound. The origins enantioselectivity diastereoselectivity investigated density functional theory study four possible enantiodetermining transition states. Consequently, first total syntheses ring-contracted naphthylisoquinoline alkaloid ancistrobrevolines A B accomplished concisely. This provides not only novel methodology strategy synthesize alkaloids but also direction advance catalytic research synthesis studies.

Язык: Английский

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Recent Advances in Catalytic Atroposelective Synthesis of Axially Chiral Quinazolinones

Catalysts, Год журнала: 2025, Номер 15(5), С. 426 - 426

Опубликована: Апрель 27, 2025

Quinazolinones, a class of nitrogen-containing heterocyclic compounds, occupy crucial position in medicinal chemistry and materials science due to their significant application potential. In recent years, the catalytic asymmetric synthesis axially chiral quinazolinones has emerged as prominent research area, driven by prospective applications development bioactive molecules, design ligands, fabrication functional materials. This review comprehensively summarizes advancements quinazolinones, with particular focus on construction strategies for three major structural types: C–N axis, N–N C–C axis. Key synthetic methodologies, including atroposelective halogenation, kinetic resolution, condensation–oxidation, photoredox deracemization, are discussed detail. addition, provides an in-depth analysis various systems, such peptide catalysis, enzymatic metal phosphoric acid others. Despite substantial progress made thus far, several challenges remain, expansion substrate scope, enhanced control over stereoselectivity, further exploration practical applications, drug discovery catalysis. These insights expected guide future towards novel strategies, diversification variants, comprehensive understanding biological activities functions. Ultimately, this will foster continued growth evolution rapidly advancing field.

Язык: Английский

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Metallaphotoredox Synthesis of Axially Chiral Tetrasubstituted Allenes through Regio- and Enantioselective 1,4-Carbocyanation of 1,3-Enynes

ACS Catalysis, Год журнала: 2024, Номер 14(18), С. 14048 - 14057

Опубликована: Сен. 10, 2024

Язык: Английский

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