Palladium-catalyzed highly chemoselective dearomative spirocyclization of Ugi adducts: facile access to functionalized benzoazepinespiroindolenines with diastereoselectivity

An efficient palladium-catalyzed post-Ugi dearomative cyclization has been achieved, enabling the rapid assembly of diverse benzoazepinespiroindolenine derivatives with excellent chemoselectivity and good diastereoselectivity. This methodology can controllably introduce functionality and complexity...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-10, Vol.10 (20), p.5083-5091
Main Authors: Chuan-Hua Qu, Shu-Ting, Li, Jian-Bo, Liu, Dian-Yong Tang, Zhi-Gang Xu, Zhong-Zhu, Chen, Gui-Ting, Song
Format: Article
Language:English
Subjects:
Adducts
Complexity
Density functional theory
Functional groups
Organic chemistry
Palladium
Reaction mechanisms
Stereoselectivity
Substrates
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Summary:An efficient palladium-catalyzed post-Ugi dearomative cyclization has been achieved, enabling the rapid assembly of diverse benzoazepinespiroindolenine derivatives with excellent chemoselectivity and good diastereoselectivity. This methodology can controllably introduce functionality and complexity into the dearomatized alicyclic products in a cost-effective and step-economical manner with a wide range of substrate scope. The highly precise dearomatization of complex Ugi adducts opens the door to address formidable chemoselectivity issues among nucleophilic sites, and complements the functional group compatibility of the classical dearomatization protocols. Density functional theory (DFT) calculations shed light on the reaction mechanism as well as the origin of chemoselectivity.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01262j