Issue 13, 2010
From the journal:

Organic & Biomolecular Chemistry

Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins†

Miao Ding,a   Feng Zhou,a   Zi-Qing Qiana  and  Jian Zhou*a  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, (P. R. China)
E-mail: jzhou@chem.ecnu.edu.cn
Fax: +86-21-62234560
Tel: +86-21-62234560

Abstract

Quinidine was found to catalyze the Michael addition of unprotected 3-substituted oxindoles to nitroolefins in excellent yield and moderate to good diastereoselectivity. Bifunctional quinidine derived thiourea catalyst 10 could catalyze this reaction to afford the major diastereomer in up to 85% ee.

Graphical abstract: Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins

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Article information

DOI
https://doi.org/10.1039/C004037A
Article type
Communication
Submitted
09 Mar 2010
Accepted
04 May 2010
First published
17 May 2010

Org. Biomol. Chem., 2010,8, 2912-2914

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Organocatalytic Michael addition of unprotected 3-substituted oxindoles to nitroolefins

M. Ding, F. Zhou, Z. Qian and J. Zhou, Org. Biomol. Chem., 2010, 8, 2912 DOI: 10.1039/C004037A

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