Issue 81, 2017
From the journal:

Chemical Communications

Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence†

Yanshuo Zhu,a   Jing Zhou, ORCID logo b   Shaojing Jin,a   Huahui Dong,a   Jiaomei Guo,a   Xuguan Bai,a   Qilin Wang ORCID logo *a  and  Zhanwei Bu*a  

* Corresponding authors

a College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, China
E-mail: wangqilin@henu.edu.cn, buzhanwei@henu.edu.cn

b School of Pharmaceutical Science, Chongqing Research Center for Pharmaceutical Engineering, Chongqing Medical University University, Chongqing 400016, China

Abstract

A TfOH-catalyzed highly diastereoselective Michael addition/ketalization sequence of 3-hydroxyoxindoles and ortho-hydroxychalcones was developed, leading to biologically important bridged ketal spirooxindoles in moderate to excellent yields. Moreover, some chemical transformations were carried out to further extend the structural complexity and diversity.

Graphical abstract: Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence

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Article information

DOI
https://doi.org/10.1039/C7CC05813F
Article type
Communication
Submitted
26 Jul 2017
Accepted
21 Sep 2017
First published
21 Sep 2017

Chem. Commun., 2017,53, 11201-11204

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Metal-free diastereoselective construction of bridged ketal spirooxindoles via a Michael addition-inspired sequence

Y. Zhu, J. Zhou, S. Jin, H. Dong, J. Guo, X. Bai, Q. Wang and Z. Bu, Chem. Commun., 2017, 53, 11201 DOI: 10.1039/C7CC05813F

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