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Issue 1, 2018
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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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Article information


Submitted
04 Aug 2017
Accepted
19 Sep 2017
First published
20 Sep 2017

Org. Chem. Front., 2018,5, 70-74
Article type
Research Article

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., 2018, 5, 70
DOI: 10.1039/C7QO00691H

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