Recent advances of Pd-π-allyl zwitterions in cycloaddition reactions

Chinese Chemical Letters, Год журнала: 2023, Номер 34(11), С. 108401 - 108401

Опубликована: Март 30, 2023

Язык: Английский

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Recent progress in the construction of eight-membered nitrogen-heterocycles

New Journal of Chemistry, Год журнала: 2024, Номер 48(11), С. 4645 - 4669

Опубликована: Янв. 1, 2024

This review summarized the progress in synthesizing eight-membered N-heterocycles over past two decades (1995–2023), inspiring synthetic chemists to develop more efficient strategies for construction of these skeletons.

Язык: Английский

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Palladium-Catalyzed Ligand-Directed Divergent Decarboxylative Cycloadditions of Vinyloxazolidine-2,4-diones with 1,3,5-Triazinanes

Organic Letters, Год журнала: 2024, Номер 26(8), С. 1589 - 1594

Опубликована: Фев. 22, 2024

This study demonstrates a highly efficient regiodivergent ligand-controlled palladium-catalyzed cycloaddition reaction of vinyloxazolidine-2,4-diones with 1,3,5-triazinanes. In the presence diphosphine ligand, proceeds via (5+2) pathway to afford 1,3-diazepin-4-ones in excellent yields, while using monophosphine smoothly (3+2) give imidazolidin-4-ones good yields.

Язык: Английский

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Catalyst-Controlled Switchable (5 + 4)/(3 + 4) Cycloadditions for the Divergent Synthesis of Pyrazole-Fused Seven- and Nine-Membered Heterocycles

ACS Catalysis, Год журнала: 2023, Номер 13(16), С. 10694 - 10704

Опубликована: Авг. 1, 2023

Developing diversity-oriented synthetic approaches for medium-sized rings is of great interest, and the divergent synthesis with different ring sizes poses a challenging task. In this study, we present catalyst-controlled switchable (5 + 4)/(3 4) cycloaddition strategy seven- nine-membered heterocycles. Utilizing two 4-aminopyridine Lewis base catalysts, pyrazole-fused benzazepines or benzoxazonines can be efficiently assembled from same substrates. These products exhibit good stability without interconversion under reaction conditions elevated temperatures. The origin chemoselectivity was elucidated by means computational studies involving DFT calculations, distortion/interaction analysis, noncovalent interaction analysis.

Язык: Английский

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Pd-catalyzed exclusively regioselective [5 + 4] cycloaddition for the construction of 1,5-di/ox-azonanes

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(7), С. 1680 - 1685

Опубликована: Янв. 1, 2023

An efficient approach for the exclusively regioselective construction of 1,5-di/ox-azonanes via Pd-catalyzed [5 + 4] cycloaddition has been developed.

Язык: Английский

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Rapidly diastereoselective assembly of ten-membered N-heterocycles between two 1,3-dipoles and their diversity to access fused N-heterocycles

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110207 - 110207

Опубликована: Июль 1, 2024

Язык: Английский

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Stereoselective construction of azepine-containing bridged scaffolds via organocata-lytic bicyclization of yne-allenone esters with nitrones

Chinese Chemical Letters, Год журнала: 2022, Номер 34(4), С. 107751 - 107751

Опубликована: Авг. 23, 2022

Язык: Английский

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Enantioselective Synthesis of Ten-Membered Lactones via Palladium-Catalyzed [5 + 5] Annulation

Organic Letters, Год журнала: 2023, Номер 25(12), С. 2030 - 2035

Опубликована: Март 20, 2023

Ten-membered lactones are the core units of many biologically active natural products but with a great synthetic challenge. Based on principle vinylogy, novel types cyclic vinylogous anhydrides have been designed as five-carbon carbonyl synthons, further applied in [5 + 5] annulation vinylethylene carbonates under chiral palladium catalysis. This strategy features excellent regioselectivity, mild conditions, and broad substrate scope, affording range spiro ten-membered bearing oxindole pyrrolidinone motif yield (up to 99%) moderate high enantioselectivity 89% ee).

Язык: Английский

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Controlled generation of ortho-quinone methides and (4+3) cyclization with 2-indolylalcohols by dual photoredox/Brønsted acid relay catalysis

Green Synthesis and Catalysis, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Given the significance of oxacyclic frameworks in molecular scaffolds and drug discovery, it is intriguing to precisely construct manipulate such ring systems chemical research. In this area, intermolecular, multicomponent cyclization for synthesis diversely substituted seven-membered oxacycles under simple conditions still a challenge. Here, we report dual photoredox/Brønsted acid relay catalytic strategy situ generation ortho-quinone methides subsequent (4+3) with 2-indolylalcohols. one-pot reaction, two C-C one C-O bonds are formed, providing de novo access various biologically important indole-fused, oxygen-containing heterocycles. By virtue chiral phosphoric acid, an asymmetric version can also be achieved good excellent levels enantioselectivity (up 96:4 er).

Язык: Английский

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Divergent Synthesis of Dihydrofuran and Dienol Scaffolds via Pd-Catalyzed Decarboxylative Carbene Cross-Coupling

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Апрель 24, 2025

Herein, we report a novel ligand-switchable Pd-catalyzed carbene coupling reaction employing vinylethylene carbonates and sulfoxonium ylides. By proper choice of ligands, the chemoselectivity process could be efficiently regulated, allowing for availability dihydrofuran or dienol scaffolds. This method features mild conditions, broad scope, remarkable synthetic utility. Compound 6f can effectively stimulate secretion GLP-1, providing promising insight into development small-molecule agonists GLP-1 receptor.

Язык: Английский

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