Issue 42, 2012
From the journal:

Chemical Communications

Bicyclic guanidine-catalyzed asymmetric Michael additions of 3-benzyl-substituted oxindoles to N-maleimides†

Lixin Li,a   Wenchao Chen,a   Wenguo Yang,a   Yuanhang Pan,b   Hongjun Liu,b   Choon-Hong Tan*ab  and  Zhiyong Jiang*a  

* Corresponding authors

a Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Kaifeng, Henan, People's Republic of China
E-mail: chmjzy@henu.edu.cn

b Department of Chemistry, National University of Singapore (NUS), 3 Science Drive 3, Singapore
E-mail: chmtanch@nus.edu.sg

Abstract

A bicyclic guanidine-catalyzed Michael addition of 3-benzyl substituted oxindoles to N-maleimides has been developed to produce oxindole derivatives with a quaternary carbon chiral center at the 3-position in excellent yields and enantio- and diastereoselectivities. This is the first incorporation of N-benzylic α-branched succinimides into 3,3-disubstituted oxindoles.

Graphical abstract: Bicyclic guanidine-catalyzed asymmetric Michael additions of 3-benzyl-substituted oxindoles to N-maleimides

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2CC31587D
Article type
Communication
Submitted
02 Mar 2012
Accepted
20 Mar 2012
First published
20 Mar 2012

Chem. Commun., 2012,48, 5124-5126

Permissions

Request permissions

Bicyclic guanidine-catalyzed asymmetric Michael additions of 3-benzyl-substituted oxindoles to N-maleimides

L. Li, W. Chen, W. Yang, Y. Pan, H. Liu, C. Tan and Z. Jiang, Chem. Commun., 2012, 48, 5124 DOI: 10.1039/C2CC31587D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements