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Issue 96, 2018
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Stereogenic cis-2-substituted-N-acetyl-3-hydroxy-indolines via ruthenium(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation

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Abstract

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).

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

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Publication details

The article was received on 10 Sep 2018, accepted on 10 Oct 2018 and first published on 11 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07336H
Citation: Chem. Commun., 2018,54, 13503-13506
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    Stereogenic cis-2-substituted-N-acetyl-3-hydroxy-indolines via ruthenium(II)-catalyzed dynamic kinetic resolution-asymmetric transfer hydrogenation

    Z. Luo, G. Sun, Z. Zhou, G. Liu, B. Luan, Y. Lin, L. Zhang and Z. Wang, Chem. Commun., 2018, 54, 13503
    DOI: 10.1039/C8CC07336H

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