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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Palladium-Catalyzed (4 + 1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(12), С. 8951 - 8959

Опубликована: Май 30, 2024

Palladium-catalyzed (4 + 1) annulation of 4-vinylbenzodioxinones with sulfur ylides has been developed to afford various dihydrobenzofuran derivatives in moderate high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating application potential current organic synthesis.

Язык: Английский

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A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones: access to ten-membered N,O-containing heterocycles

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(15), С. 4131 - 4137

Опубликована: Янв. 1, 2024

A palladium-catalyzed decarboxylative (5 + 5) cyclization reaction of vinyloxazolidine-2,4-diones for the synthesis ten-membered N,O-containing heterocycles is disclosed.

Язык: Английский

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Palladium-Catalyzed [3 + 2] Cycloaddition of 4-Vinyl-4-Butyrolactones with Alkenes: Synthesis of Spirocyclopentane Compounds

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

Опубликована: Сен. 12, 2024

A palladium-catalyzed [3 + 2] cycloaddition of 4-vinyl-4-butyrolactones (VBLs) with alkenes has been developed to afford various spirocyclopentane products in high yields excellent diastereoselectivities. The scale-up reaction and further derivations the product worked well, demonstrating potential application current organic synthesis.

Язык: Английский

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SnCl₂ Catalyzed Multicomponent Coupling: Synthesis of 1,3-Oxazolidine Derivatives Using Paraformaldehyde as a C1 Feedstock

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(28), С. 5768 - 5775

Опубликована: Янв. 1, 2024

SnCl

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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Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles

Chemical Communications, Год журнала: 2024, Номер 60(76), С. 10516 - 10519

Опубликована: Янв. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Язык: Английский

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Palladium-Catalyzed [3+2] Cycloaddition of 4-Vinyl-4-Butyro-lactones with Sulfamate-Derived Cyclic Imines: Construction of Sulfamate-Fused Pyrrolidines

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

The palladium-catalyzed [3 + 2] decarboxylative cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines has been developed, providing the sulfamate-fused pyrrolidine derivatives in high yields good diastereoselectivities.

Язык: Английский

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