Issue 20, 2023

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

Abstract

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 ago 2023
Accepted
09 set 2023
First published
11 set 2023

Org. Chem. Front., 2023,10, 5083-5091

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

C. Qu, S. Li, J. Liu, D. Tang, Z. Xu, Z. Chen and G. Song, Org. Chem. Front., 2023, 10, 5083 DOI: 10.1039/D3QO01262J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements