Direct catalytic asymmetric vinylogous Michael addition to construct an all-carbon quaternary center with 3-alkenyl-oxindoles

The first highly enantioselective asymmetric vinylogous Michael addition of α,α-dicyanoalkenes with 3-alkenyl-oxindoles catalyzed by chiral-at-metal complexes to deliver 3,3′-disubstituted oxindole bearing an all-carbon quaternary stereocenter has been developed. In the presence of 1.0 mol% of chira...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-06, Vol.9 (13), p.3446-3451
Main Authors: Lu, Shuhui, Zhao, Zhifei, Ren, Yingzheng, Du, Guangfen, Zhao, Jixing, Shi-Wu, Li
Format: Article
Language:English
Subjects:
Adducts
Asymmetry
Carbon
Coordination compounds
Enantiomers
Heterocyclic compounds
Metal complexes
Organic chemistry
Sulfur
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Summary:The first highly enantioselective asymmetric vinylogous Michael addition of α,α-dicyanoalkenes with 3-alkenyl-oxindoles catalyzed by chiral-at-metal complexes to deliver 3,3′-disubstituted oxindole bearing an all-carbon quaternary stereocenter has been developed. In the presence of 1.0 mol% of chiral Rh(iii) complex, corresponding adducts were obtained in 21–98% yields with 80–97% ee. Remarkably, this protocol exhibited excellent advantages in terms of enantioselectivity, given the fact that as low as 0.05 mol% of chiral Rh(iii) complex could promote the title reaction on a gram scale to afford the desired product with excellent enantiomer excess values. In addition, the utility of this approach was verified by the formal synthesis of sulfur-containing heterocyclic compounds.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00223j