Synthesis of Medium-Sized Rings by Z-Retentive Asymmetric Allylic Substitution-Enabled Intermolecular Cascade Cyclization under Iridium/Cinchona Catalysis

ACS Catalysis, Год журнала: 2024, Номер 14(20), С. 15743 - 15750

Опубликована: Окт. 9, 2024

Medium-sized rings are important structural units in organic molecules of significant interest. However, their efficient synthesis, especially a highly enantioselective manner, has been formidable challenge. Herein, we report an synthesis medium-sized aza-rings by Z-retentive asymmetric allylic substitution-enabled intermolecular cascade cyclization via iridium/cinchona dual catalysis. The reaction was performed under mild conditions and with good functional group tolerance. Various nine- to eleven-membered can be afforded moderate high yields (up 98%) enantioselectivities 93% ee). utilization both Z-linear dipole precursor binary catalyst is critical for the desired reactivity.

Язык: Английский

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Acid-Regulated Selective Synthesis of Benzofuran Derivatives via Single-Component BDA Retro-Aldol/Michael Addition Cascade and [4 + 2] Cycloaddition Reactions

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

Опубликована: Май 20, 2025

The acid-controlled single-component retro-aldol/Michael addition cascade reaction and [4 + 2] cycloaddition of benzofuran-derived azadienes (BDAs) are reported for the first time. Under conditions trifluoromethanesulfonic acid as catalyst with water, BDAs initiate retro-aldol reaction, followed by a 1,4-Michael addition, yielding (arylmethylene)bis(dibenzofuran) products excellent yields broad substrate applicability. This represents application in reaction. In contrast, absence water boron trifluoride etherate catalyst, undergo constructing spiro[benzofuran-2,3'-benzofuro[3,2-b]pyridine] framework high diastereoselectivity. method features mild atom economy, provides new approach benzofuran scaffold derivatives.

Язык: Английский

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Nine-Membered Ketolactams by Oxidative Cyclization Expansion

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Май 27, 2025

Considerable progress has been made over decades in synthetic organic chemistry order to build up molecular complexity, often through the design of advanced catalytic systems. Yet, simply exposing molecules benchmark oxidants catalyst free conditions can sometimes lead surprising and highly valuable products. Thus, a method for accessing rare 9-membered ketolactams is herein described, under mild oxidative conditions. Key 18O 17O label experiments revealed an unexpected oxygen atom migration event ring expansion process. The scope, mechanism, applications, 9 7 membered contraction opportunities are discussed.

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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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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Palladium/Phosphine Complex Catalyzed [4＋4] Annulations of Morita-Baylis-Hillman Carbonates and 1-Azadienes

Chinese Journal of Organic Chemistry, Год журнала: 2024, Номер 44(12), С. 3761 - 3761

Опубликована: Янв. 1, 2024

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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