Issue 32, 2014
From the journal:

Organic & Biomolecular Chemistry

Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines†

Zhongkai Tang,‡a   Yan Shi,‡a   Haibin Mao,a   Xuebin Zhu,a   Weipeng Li,a   Yixiang Cheng,a   Wen-Hua Zheng*a  and  Chengjian Zhu*ab  

* Corresponding authors

a State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, P.R. China
E-mail: cjzhu@nju.edu.cn, wzheng@nju.edu.cn

b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, CAS, Shanghai, P.R. China

Abstract

A highly efficient asymmetric organocatalytic addition of 3-substituted oxindole to isatin-derived ketimine is reported with excellent stereocontrol (>99 : 1 dr, >99% ee) under mild conditions. This method provides access to the bisoxindole structure moiety with two vicinal quaternary stereogenic centers.

Graphical abstract: Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines

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Article information

DOI
https://doi.org/10.1039/C4OB01039F
Article type
Communication
Submitted
20 May 2014
Accepted
18 Jun 2014
First published
18 Jun 2014

Org. Biomol. Chem., 2014,12, 6085-6088

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Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines

Z. Tang, Y. Shi, H. Mao, X. Zhu, W. Li, Y. Cheng, W. Zheng and C. Zhu, Org. Biomol. Chem., 2014, 12, 6085 DOI: 10.1039/C4OB01039F

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