Issue 4, 2017
From the journal:

Organic & Biomolecular Chemistry

A DBU-catalyzed Michael–Pinner–isomerization cascade reaction of 3-hydroxyoxindoles with isatylidene malononitriles: access to highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif†

Yan-Shuo Zhu,a   Wen-Bo Wang,a   Bei-Bei Yuan,a   Ya-Ning Li,a   Qi-Lin Wang ORCID logo *a  and  Zhan-Wei 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

Abstract

The first DBU-catalyzed Michael/Pinner/isomerization cascade reaction of 3-hydrooxindoles with isatylidene malononitriles was developed, and the corresponding highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif were obtained in up to 92% yields. This protocol also provides an efficient method for the synthesis of an α-cyano-γ-butyrolactone bispirooxindole. In addition, a one-pot three-component cascade reaction was conducted. Also, the asymmetric version of the cascade reaction was achieved.

Graphical abstract: A DBU-catalyzed Michael–Pinner–isomerization cascade reaction of 3-hydroxyoxindoles with isatylidene malononitriles: access to highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif

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Article information

DOI
https://doi.org/10.1039/C6OB02254E
Article type
Paper
Submitted
17 Oct 2016
Accepted
23 Dec 2016
First published
23 Dec 2016

Org. Biomol. Chem., 2017,15, 984-990

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A DBU-catalyzed Michael–Pinner–isomerization cascade reaction of 3-hydroxyoxindoles with isatylidene malononitriles: access to highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif

Y. Zhu, W. Wang, B. Yuan, Y. Li, Q. Wang and Z. Bu, Org. Biomol. Chem., 2017, 15, 984 DOI: 10.1039/C6OB02254E

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