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A copper(I)-catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines: enantioselective synthesis of 3-substituted 3-aminooxindoles

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Abstract

A Cu(I)/Ph-Phosferrox complex catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines has been described. This strategy can provide direct access to chiral 3-substituted 3-aminooxindoles bearing vicinal quaternary–tertiary carbon stereocenters in high yields (up to 99%), excellent enantioselectivities (up to >99% ee) and moderate to high diastereoselectivities (up to 98 : 2 dr).

Graphical abstract: A copper(i)-catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines: enantioselective synthesis of 3-substituted 3-aminooxindoles

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Publication details

The article was received on 04 Aug 2017, accepted on 19 Sep 2017 and first published on 20 Sep 2017


Article type: Research Article
DOI: 10.1039/C7QO00691H
Citation: Org. Chem. Front., 2017, Advance Article
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    A copper(I)-catalyzed asymmetric Mannich reaction of glycine Schiff bases with isatin-derived ketimines: enantioselective synthesis of 3-substituted 3-aminooxindoles

    J. Zhu, W. Yang, Y. Liu, S. Shang and W. Deng, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00691H

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