Issue 1, 2018
From the journal:

Organic Chemistry Frontiers

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

Jing-Yan Zhu,a   Wu-Lin Yang,*a   Yang-Zi Liu,a   Shao-Jing Shanga  and  Wei-Ping Deng ORCID logo *a  

* Corresponding authors

a School of Pharmacy and Shanghai Key Laboratory of New Drug Design, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China
E-mail: ywlecust@gmail.com, weiping_deng@ecust.edu.cn

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

DOI
https://doi.org/10.1039/C7QO00691H
Article type
Research Article
Submitted
04 aug 2017
Accepted
19 sep 2017
First published
20 sep 2017

Org. Chem. Front., 2018,5, 70-74

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

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