Issue 63, 2019
From the journal:

Chemical Communications

Highly enantioselective sequential vinylogous aldol reaction/transesterification of methyl-substituted olefinic butyrolactones with isatins for the construction of chiral spirocyclic oxindole-dihydropyranones†

Zhen-Hua Wang, ORCID logo *a   Xia-Yan Zhang,b   Chuan-Wen Lei,b   Jian-Qiang Zhao, ORCID logo a   Yong You ORCID logo a  and  Wei-Cheng Yuan ORCID logo *ab  

* Corresponding authors

a Institute for Advanced Study, Chengdu University, Chengdu 610106, China

b National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
E-mail: wangzhenhua@cdu.edu.cn, yuanwc@cioc.ac.cn

Abstract

A highly stereoselective sequential vinylogous aldol reaction/transesterification of methyl-substituted olefinic butyrolactones and isatins was developed. With this developed protocol, a series of chiral spirocyclic oxindole-dihydropyranones were obtained in good to excellent yields (73–99%) and enantioselectivities (71–97% ee).

Graphical abstract: Highly enantioselective sequential vinylogous aldol reaction/transesterification of methyl-substituted olefinic butyrolactones with isatins for the construction of chiral spirocyclic oxindole-dihydropyranones

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Article information

DOI
https://doi.org/10.1039/C9CC04427B
Article type
Communication
Submitted
10 Jun 2019
Accepted
09 Jul 2019
First published
09 Jul 2019

Chem. Commun., 2019,55, 9327-9330

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Highly enantioselective sequential vinylogous aldol reaction/transesterification of methyl-substituted olefinic butyrolactones with isatins for the construction of chiral spirocyclic oxindole-dihydropyranones

Z. Wang, X. Zhang, C. Lei, J. Zhao, Y. You and W. Yuan, Chem. Commun., 2019, 55, 9327 DOI: 10.1039/C9CC04427B

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