Issue 82, 2013
From the journal:

Chemical Communications

An organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles†

Qi-Lin Wang,ab   Lin Peng,a   Fei-Ying Wang,a   Ming-Liang Zhang,ab   Li-Na Jia,ab   Fang Tian,a   Xiao-Ying Xu*a  and  Li-Xin Wang*a  

* Corresponding authors

a Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
E-mail: wlxioc@cioc.ac.cn, xuxy@cioc.ac.cn

b University of Chinese Academy of Sciences, Beijing 10049, China

Abstract

The first organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25–85% yield, 60–94% ee and up to >20 : 1 diastereoselectivity.

Graphical abstract: An organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles

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Article information

DOI
https://doi.org/10.1039/C3CC45139A
Article type
Communication
Submitted
09 Jul 2013
Accepted
31 Jul 2013
First published
01 Aug 2013

Chem. Commun., 2013,49, 9422-9424

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An organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles

Q. Wang, L. Peng, F. Wang, M. Zhang, L. Jia, F. Tian, X. Xu and L. Wang, Chem. Commun., 2013, 49, 9422 DOI: 10.1039/C3CC45139A

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