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

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. Comp...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 9; no. 14; pp. 3697 - 3708
Main Authors Pan, Yuan, Ren, Weiwu, Zhang, Zhanhao, Luo, Fengbiao, Hou, Xiaohan, Li, Xiaoyang, Yang, Yun-Fang, Wang, Yang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 12.07.2022
Royal Society of Chemistry
Subjects
Anticancer properties
Antitumor agents
Carbon
Chemistry
Chemistry, Organic
Computer applications
Cyclopentane
Organic chemistry
Physical Sciences
Quinones
Science & Technology
Stereoselectivity
Tumors
MOLECULAR HYBRIDIZATION
COPPER-MEDIATED CONSTRUCTION
HIGHLY ENANTIOSELECTIVE CONSTRUCTION
CARBENE-CATALYZED-REACTIONS
X-RAY-ANALYSIS
4 CONSECUTIVE STEREOCENTERS
VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT
TRANSITION-METAL-FREE
CRAFTS ALLYLIC ALKYLATION
C-H
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Summary: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.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d2qo00471b