Issue 14, 2022

Tandem 1,6-addition/cyclopropanation/rearrangement reaction of vinylogous para-quinone methides with 3-chlorooxindoles: construction of vicinal quaternary carbon centers

Abstract

A novel tandem 1,6-addition/cyclopropanation/rearrangement reaction of vinylogous para-quinone methides with 3-chlorooxindoles is reported. This method provides an efficient approach to various functionalized dispirooxindole–cyclopentane–cyclohexadienones with vicinal quaternary carbon centers. Computational studies have been conducted to provide insight into the origin of diastereoselectivity and predict a stepwise diradical mechanism. The anti-tumor activities of these structurally unique dispirooxindole derivatives are also reported.

Graphical abstract: Tandem 1,6-addition/cyclopropanation/rearrangement reaction of vinylogous para-quinone methides with 3-chlorooxindoles: construction of vicinal quaternary carbon centers

Supplementary files

Article information

Article type
Research Article
Submitted
23 Mar 2022
Accepted
24 May 2022
First published
25 May 2022

Org. Chem. Front., 2022,9, 3697-3708

Tandem 1,6-addition/cyclopropanation/rearrangement reaction of vinylogous para-quinone methides with 3-chlorooxindoles: construction of vicinal quaternary carbon centers

Y. Pan, W. Ren, Z. Zhang, F. Luo, X. Hou, X. Li, Y. Yang and Y. Wang, Org. Chem. Front., 2022, 9, 3697 DOI: 10.1039/D2QO00471B

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