Diastereo- and Enantioselective Construction of Dihydroisocoumarin-Based Spirooxindole Frameworks via Organocatalytic Tandem Reactions

An organocatalytic asymmetric approach has been developed for the ennantioselective construction of dihydroisocoumarin‐based spirooxindole frameworks in high yields, excellent diastereo‐ and enantioselectivities (up to 99%, all >95:5 dr, up to 99% ee). This approach takes advantage of chiral thio...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-09, Vol.358 (17), p.2777-2790
Main Authors: Wu, Jia-Le, Du, Bai-Xiang, Zhang, Yu-Chen, He, Ying-Ying, Wang, Jing-Yi, Wu, Ping, Shi, Feng
Format: Article
Language:English
Subjects:
Anhydrides
asymmetric organocatalysis
Asymmetry
Cascade chemical reactions
Catalysis
Catalysts
Chemical synthesis
Construction methods
dihydroisocoumarins
Enantiomers
enantioselectivity
spirooxindoles
Substrates
Synthesis
Synthesis (chemistry)
tandem reactions
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Summary:An organocatalytic asymmetric approach has been developed for the ennantioselective construction of dihydroisocoumarin‐based spirooxindole frameworks in high yields, excellent diastereo‐ and enantioselectivities (up to 99%, all >95:5 dr, up to 99% ee). This approach takes advantage of chiral thiourea‐tertiaryamine catalyzed tandem reaction of isatins with enolizable homophthalic anhydride, which has wide substrate scope and can be performed with low catalyst loading. This reaction not only provides an efficient and useful method for constructing enantioenriched dihydroisocoumarin‐based spirooxindole scaffold, but also will enrich the research contents of catalytic asymmetric tandem reactions and enantioselective synthesis of biologically important spirooxindoles.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600271