Dearomative (3 + 2) Cycloadditions of 3-Nitroheteroarenes with Allenyl Sulfones Mediated by Ion Pair Organocatalysis

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 8, 2025

We report the first example of dearomative (3 + 2) cycloadditions 3-nitro(aza)-indole, -benzofuran, and -benzothiophene derivatives in presence allenyl sulfones, using sulfinate ammonium ion pairs as organocatalytic promoters. The methodology provides a new, facile, efficient protocol for synthesis functionalized 2,3-fused cyclopentannulated indolines dihydrobenzofurans.

Язык: Английский

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Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Фев. 10, 2025

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.

Язык: Английский

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Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightfor-ward Access to the (thio)Hydantoin Scaffold

Опубликована: Апрель 26, 2024

A palladium-catalyzed (3+2) cycloaddition between 5-vinyloxazolidine-2,4-diones (VOxD) and (thio)isocyanates is described. Under optimized conditions, an array of (thio)hydantoins was readily prepared enantioselective version this transformation then studied. To illustrate the importance method, a concise synthesis two bioactive compounds, nirvanol mephenytoin, carried out. This work emphasizes synthetic potential VOxD as useful precursors zwitterionic aza-π- allylpalladium II intermediates.

Язык: Английский

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Cycloadditions of 5-Vinyloxazolidine-2,4-diones: A Straightforward Access to the (Thio)hydantoin Scaffold

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(17), С. 12370 - 12377

Опубликована: Авг. 24, 2024

A palladium-catalyzed (3 + 2) cycloaddition between 5-vinyloxazolidine-2,4-diones (VOxD) and (thio)isocyanates is described. Under optimized conditions, an array of (thio)hydantoins was readily prepared, enantioselective version this transformation then studied. To illustrate the importance method, a concise synthesis two bioactive compounds, nirvanol mephenytoin, carried out. This work emphasizes synthetic potential VOxD as useful precursors zwitterionic aza-π-allylpalladiumII intermediates.

Язык: Английский

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Construction of Sulfur(IV)‐Chiral Six‐Membered Heterocycles by Pd‐Catalyzed Asymmetric (4+2) Dipolar Cyclization

European Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 27, 2024

Abstract Chiral sulfur‐containing compounds play an important role in asymmetric catalysis and synthesis, chiral pharmaceuticals, materials. While great progress has been made the synthesis of these compounds, catalytic heterocycles remains relatively limited compared to acyclic ones. In this study, we successfully report efficient highly selective structurally diverse chirality‐at‐sulfur(IV) six‐membered under mild conditions via a Pd‐catalyzed (4+2) dipolar cyclization. More importantly, products enable enantioselective preparation variety other S‐stereogenic derivatives.

Язык: Английский

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Recent Advances in Palladium-Catalyzed Annulations for the Synthesis of Pyrrolidines

Journal of Molecular Structure, Год журнала: 2024, Номер unknown, С. 141010 - 141010

Опубликована: Дек. 1, 2024

Язык: Английский

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