Oxidative spirolactonisation for modular access of γ-spirolactones via a radical tandem annulation pathway

An oxidative annulation of 2-arylidene-1,3-indanediones with Meldrum's acid has been developed for the divergent syntheses of spirolactones with a spirocenter located at the γ-position with respect to the carbonyl group. This heteroannulation protocol tolerates various functional groups and del...

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Veröffentlicht in:Chinese chemical letters 2024-10, Vol.35 (10), p.109565, Article 109565
Hauptverfasser: Duan, Jindian, Ding, Xiaojuan, Choy, Pui Ying, Xu, Binyan, Li, Luchao, Qin, Hong, Fang, Zheng, Kwong, Fuk Yee, Guo, Kai
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Sprache:eng
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Zusammenfassung:An oxidative annulation of 2-arylidene-1,3-indanediones with Meldrum's acid has been developed for the divergent syntheses of spirolactones with a spirocenter located at the γ-position with respect to the carbonyl group. This heteroannulation protocol tolerates various functional groups and delivers moderate-to-good product yields. Interestingly, the reaction outcomes are exclusively controlled by the reaction oxidant/medium. This annulation strategy can also be executed in the flow system with decent product yields. Control experiments revealed that the reaction proceeds via a radical tandem annulation pathway. An oxidative annulation of 2-arylidene-1,3-indanediones with Meldrum's acid has been developed for the divergent syntheses of spirolactones with a spirocenter located at the γ-position with respect to the carbonyl group. [Display omitted]
ISSN:1001-8417
DOI:10.1016/j.cclet.2024.109565