A zinc/PyBisulidine catalyzed asymmetric Mannich reaction of N-tosyl imines with 3-acyloxy-2-oxindoles

A Zn-PyBisulidine catalyzed asymmetric Mannich reaction of 3-acyloxy-2-oxindoles has been developed. Various quaternary substituted 3-acyloxy-2-oxindoles bearing vicinal amino alcohol motifs were obtained in good to excellent yields with moderate to excellent dr and excellent enantioselectivities. T...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-09, Vol.19 (34), p.7460-7469
Main Authors: Yang, Zinan, He, Huakang, Tian, Rui, Wu, Ruoran, Hu, Sheng, Wu, Yue, Zhou, Hui
Format: Article
Language:English
Subjects:
Asymmetry
Crystallography
Enantiomers
High-performance liquid chromatography
Imines
Liquid chromatography
NMR
Nuclear magnetic resonance
Optimization
Zinc
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Summary:A Zn-PyBisulidine catalyzed asymmetric Mannich reaction of 3-acyloxy-2-oxindoles has been developed. Various quaternary substituted 3-acyloxy-2-oxindoles bearing vicinal amino alcohol motifs were obtained in good to excellent yields with moderate to excellent dr and excellent enantioselectivities. The utility of this reaction was demonstrated by the easy removal of the acyl group to give C3-hydroxy derivatives and their application as a key skeleton of the ligand for the Ni-catalyzed enantioselective Henry reaction.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01328a