Stereogenic cis-2-substituted-N-acetyl-3-hydroxy-indolines via ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation

Ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation of racemic 2-substituted-N-acetyl-3-oxoindolines to cis-2-substituted-N-acetyl-3-hydroxyindolines is reported. Using the homochiral {Ru[TfDPEN](p-cymene)} catalyst with S/C = 400 in a HCO2H/Et3N mixture, up to >9...

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Published in:Chemical communications (Cambridge, England) England), 2018-11, Vol.54 (96), p.13503-13506
Main Authors: Luo, Zhonghua, Sun, Guodong, Zhou, Zihong, Liu, Guozhu, Luan, Baolei, Lin, Yicao, Zhang, Lei, Wang, Zhongqing
Format: Article
Language:English
Subjects:
Asymmetry
Crystallography
Direct reduction
Heterocyclic compounds
Hydrogenation
Ruthenium
Ruthenium compounds
Substitutes
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Summary:Ruthenium(ii)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation of racemic 2-substituted-N-acetyl-3-oxoindolines to cis-2-substituted-N-acetyl-3-hydroxyindolines is reported. Using the homochiral {Ru[TfDPEN](p-cymene)} catalyst with S/C = 400 in a HCO2H/Et3N mixture, up to >99.9% ee and >99 : 1 dr are obtained with high yields (79-98%). This method provides the first example of preparing enantiomerically pure indolines through asymmetric transfer hydrogenation (ATH).
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc07336h