Facile Access to Saccharin‐Fused 1,4‐Dihydropyridines through [3+3] Annulation Reactions

An efficient approach to saccharin‐fused 1,4‐DHPs has been established by using a [3+3] annulation process. The chemical event was enabled by a Et3N‐catalyzed tandem Michael/aza‐Pinner reaction of alkyl cyclic N‐sulfonyl ketimines as nucleophiles with α,α‐dicyanoolefins. Under mild conditions, the d...

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Veröffentlicht in:European journal of organic chemistry 2022-02, Vol.2022 (7), p.n/a
Hauptverfasser: Xu, Zhi‐Hua, Jia, Shi‐Kun, Chang, Zhe‐Ran, Hua, Yuan‐Zhao, Wang, Min‐Can, Mei, Guang‐Jian
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Sprache:eng
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Zusammenfassung:An efficient approach to saccharin‐fused 1,4‐DHPs has been established by using a [3+3] annulation process. The chemical event was enabled by a Et3N‐catalyzed tandem Michael/aza‐Pinner reaction of alkyl cyclic N‐sulfonyl ketimines as nucleophiles with α,α‐dicyanoolefins. Under mild conditions, the desired products were readily prepared in good to excellent yields and with broad functional group tolerance (up to 95 % yield, 29 examples). Notably, this practical methodology features the synthesis of pentacyclic spirooxindoles bearing a quaternary spiro‐stereocenter. An efficient [3+3] annulation reaction of cyclic N‐sulfonyl ketimine and α,α‐dicyanoolefins has been developed via a Et3N‐catalyzed tandem Michael/aza‐Pinner process, affording a broad range of saccharine‐fused 1,4‐DHPs in good to excellent yields (up to 95 %).
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202101423