Diastereodivergent synthesis of bispirooxindoles via asymmetric Friedel-Crafts/aldol cascade reaction: co-catalyst effects on diastereoselective outcomes

A combination of metal- and organo-catalysts sequentially catalyzing the Friedel-Crafts/aldol tandem reaction between 3-pyrrolyl-oxindoles and isatin-derived β,γ-unsaturated α-ketoesters has been reported, which leads to two types of diastereomeric enantio-enriched bispirooxindoles with three quater...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018-03, Vol.54 (18), p.2260-2263
Main Authors: Li, Nai-Kai, Fan, Wei-Tai, Zhang, Jun-Qi, Sun, Bing-Bing, Chen, Jun-Bo, Wang, Xing-Wang
Format: Article
Language:English
Subjects:
Aldehydes
Cascade chemical reactions
Catalysis
Catalysts
Chemical synthesis
Friedel-Crafts reaction
Functional groups
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Summary:A combination of metal- and organo-catalysts sequentially catalyzing the Friedel-Crafts/aldol tandem reaction between 3-pyrrolyl-oxindoles and isatin-derived β,γ-unsaturated α-ketoesters has been reported, which leads to two types of diastereomeric enantio-enriched bispirooxindoles with three quaternary stereocentres and synthetically valuable functional groups in high yields with excellent enantioselectivity and diastereoselectivity.
ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc09489b