Catalytic atroposelective synthesis of indolyl quinazolinones bearing N–N/C–C diaxes

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 9, 2025

Language: Английский

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Atroposelective [4+1] Annulation for the Synthesis of Isotopic Isoindolinones Bearing both Central and Axial Chirality

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Isotopically chiral molecules have drawn much attention due to their practical applications in drug discovery. However, existing studies this area are mainly limited centrally and H/D exchange. Herein, we report a phosphoric acid-catalyzed atroposelective [4+1] annulation of ketoaldehydes 1H-indol-1-amines. By means strategy, series D- 18O-labeled atropisomers featuring both central axial chiralities synthesized with high enantioselectivities diastereoselectivities good excellent isotopic incorporation. Experimental density functional theory suggest that the reaction involves sequential condensation, cyclization isomerization cascade, which second step is enantio-determining process.

Language: Английский

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Trifluoromethyl Group (CF₃) Induced Regioselective Larock Indole Synthesis from Unsymmetric β-CF₃-1,3-enynes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 24, 2025

The indole skeleton exists widely in natural products, pharmaceuticals, and materials. We disclose here a trifluoromethyl group induced regioselective Larock synthetic method from unsymmetric 2-CF3-1,3-enynes. presence of is determinable for the regioselectivity. Once CF3 was replaced with methyl or phenyl group, ratio 1:1 to 1:1.4 isomers were obtained. This strategy features good regioselectivity, broad substrate scope, high functional tolerance. protocol reported offers an alternative solution rare 3,4-functionalization products further transformed show distinctive reactivity hydroboration–oxidation hydro-bromination.

Language: Английский

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Recent Advances in Palladium-Catalyzed Enantioselective Cyclization for the Construction of Atropisomers

Catalysts, Journal Year: 2025, Volume and Issue: 15(4), P. 320 - 320

Published: March 27, 2025

Axially chiral structures have become increasingly common in modern materials and pharmaceuticals, especially as ligands organocatalysts, highlighting their growing significance. In the field of pharmaceutical research, there are several notable examples worth highlighting, such antibiotics vancomycin, Knipholone, Mastigophorene A. Over past decade, availability axially compounds has significantly improved through advancements existing strategies introduction catalytic atroposelective synthesis concepts. These synthetic not only broaden scope chemical reactions, but also facilitate construction frameworks with high application value. Currently, various methods available for achieving stereoselective under catalyst control, including desymmetrization, (dynamic) kinetic resolution, cross-coupling de novo ring-forming synthesis. This paper focuses on recent advances constructing atropisomers palladium-catalyzed asymmetric cyclization strategies.

Language: Английский

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Palladium-Catalyzed Asymmetric Larock Isoquinoline Synthesis to Access Axially Chiral 3,4-Disubstituted Isoquinolines

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(40), P. 27809 - 27818

Published: Sept. 26, 2024

Larock isoquinoline synthesis is one of the most efficient and straightforward approaches to construction 3,4-disubstituted isoquinolines. However, there have been no asymmetric versions for axially chiral isoquinolines since their initial report in 2001. Herein, we documented first example an by employing Pd(OAc)

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6586 - 6590

Published: July 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).

Language: Английский

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Site Specific C3‐Alkenylation of Indoles Mediated by in situ C‐H Iodination

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 29, 2024

Abstract The C3‐alkenylation of indoles have been developed by means a novel in situ iodination tactic which is capable mediating the Heck coupling with alkenes. method features specific site‐selectivity oriented C−I bond, high‐step efficiency without pre‐functionalization for C‐halogen bond construction, as well highly general tolerance to different terminal alkenes, including unactivated acrylates, acrylic acid, vinyl sulfone functionalized natural products.

Language: Английский

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Site-Selective Electrophilic Trifluoromethylthiolation for the Synthesis of C5- or C7-SCF₃-Substituted Indolines

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence any catalyst or additive, C5-selective could proceed at room temperature. With palladium used as catalyst, selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products. This reaction features good functional group tolerance, simple operation, mild conditions, scale-up application. The potential utilities products were shown by further transformations.

Language: Английский

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