Issue 16, 2013
From the journal:

Chemical Communications

An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst†

Qiao Chen,a   Jinyan Liang,a   Shoulei Wang,a   Dong Wanga  and  Rui Wang*ab  

* Corresponding authors

a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou, China

b State Key Laboratory of Chiroscience, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong, China
E-mail: wangrui@lzu.edu.cn

Abstract

The first organocatalytic Michael–cyclization cascade reaction between isothiocyanato oxindoles and unsaturated pyrazolones has been developed. The multicyclic spiro[oxindole/thiobutyrolactam/pyrazolone] core structures containing three contiguous stereogenic centers, including two spiro quaternary centers, were prepared with excellent diastereo- (up to >20 : 1) and enantioselectivities (up to 99% ee).

Graphical abstract: An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst

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Article information

DOI
https://doi.org/10.1039/C3CC38386E
Article type
Communication
Submitted
21 Nov 2012
Accepted
07 Jan 2013
First published
08 Jan 2013

Chem. Commun., 2013,49, 1657-1659

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An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst

Q. Chen, J. Liang, S. Wang, D. Wang and R. Wang, Chem. Commun., 2013, 49, 1657 DOI: 10.1039/C3CC38386E

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