DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes DOI

Dongqiu Li,

Jiale Wu, Lulu Yang

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 20, 2024

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, use the β- ε-carbons for bond formation, presenting new regiodivergent C4 synthons Lewis base-catalyzed annulations.

Язык: Английский

Phosphine‐Catalyzed Divergent γ,γ‐ and ε,γ‐Umpolung Domino Additions of Bisoxindoles with Allenoates: Construction of Vicinal All‐Carbon Quaternary Stereocenters and Formal Total Synthesis of Dimeric Cyclotryptamine Alkaloids DOI Open Access
Yufei Zhang, Jing Chen, Hui Yao

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 25, 2025

Comprehensive Summary Vicinal all‐carbon quaternary stereocenters are widely present in natural products and bioactive molecules. However, the construction of such motif one step from readily available starting materials remains a significant challenge. Herein, we report phosphine‐catalyzed divergent γ,γ‐ ε,γ‐umpolung domino addition bisoxindoles with allenoates. This method serves as practical tool for concise synthesis series bisoxindole derivatives bearing sterically hindered vicinal under mild reaction conditions. The applicability this novel was demonstrated gram‐scale three known advanced intermediates total syntheses calycanthine, chimonanthine folicanthine.

Язык: Английский

Процитировано

3

Phosphine-Catalyzed Cascade Cycloaddition of Vinyl Oxiranes with Sulfonium Compounds to Step-Economically Construct Spiro-2(3H)-furanone Scaffolds DOI
Thomas P. Yang, Wei Du,

Chia‐Yu Wu

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 9, 2025

In this work, we developed a phosphine-catalyzed cascade lactonization/[2 + 1] annulation reaction between vinyl oxiranes and sulfonium compounds for the highly diastereoselective construction of spiro-2(3H)-furanone skeletons. The cycloaddition proceeds via 2(5H)-furanone phosphonium intermediate, introducing an oxygen-containing active intermediate phosphine catalysis. These findings highlight significant potential harnessing as versatile synthons constructing spirocyclic through simultaneous multicyclic skeleton formation.

Язык: Английский

Процитировано

0

Recent advances in phosphine-mediated sequential annulations DOI

Xuling Pan,

Wei Cai, You Huang

и другие.

Chinese Chemical Letters, Год журнала: 2024, Номер unknown, С. 110628 - 110628

Опубликована: Ноя. 1, 2024

Язык: Английский

Процитировано

1

Cascade Alkynyl Prins Cyclization and Aza-Michael Reaction: En Route to Regioselective Pyrano- and Isochromenoquinoline Scaffolds DOI
Subhamoy Biswas, Anil K. Saikia

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

Опубликована: Сен. 20, 2024

A metal-free, Lewis acid approach for the regioselective synthesis of dihydropyranoquinoline scaffolds has been unveiled. The methodology employs a cascade alkynyl Prins-aza-Michael reaction sequence to deliver products in good excellent yields. strategy features mild conditions, broad substrate scope, and high functional group tolerance. protocol further extended include isochromenoquinoline derivatives. utility lies highly fused polycyclic N,O-heterocycles via intramolecular Heck coupling. Additionally, Rh(III)-catalyzed annulation results formation fluorescent pentacyclic ammonium salts Photophysical studies reveal that these exhibit strong emission green region (500-550 nm).

Язык: Английский

Процитировано

0

DMAP-Catalyzed [4 + 2] Annulation of Hex-5-en-2-ynoates with Electron-Poor Alkenes DOI

Dongqiu Li,

Jiale Wu, Lulu Yang

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 20, 2024

Herein, we report a DMAP-catalyzed [4 + 2] annulation reaction of hex-5-en-2-ynoates 1 with electron-poor alkenes 2, which affords exocyclic olefinic cyclohexenes 3 in good yields and excellent regio-, diastereo-, E/Z selectivities. Distinguished from previous allenoate- or alkynoate-based substrates, use the β- ε-carbons for bond formation, presenting new regiodivergent C4 synthons Lewis base-catalyzed annulations.

Язык: Английский

Процитировано

0