Issue 9, 2013
From the journal:

Organic & Biomolecular Chemistry

An organocatalytic asymmetric double Michael cascade reaction of unsaturated ketones and unsaturated pyrazolones: highly efficient synthesis of spiropyrazolone derivatives†

Jinyan Liang,a   Qiao Chen,a   Luping Liu,a   Xianxing Jianga  and  Rui Wang*ab  

* Corresponding authors

a Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Life Sciences, School of Basic Medical Sciences, School of Pharmacy, State Key Laboratory of Applied Organic Chemistry and Institute of Biochemistry and Molecular Biology, Lanzhou University, Lanzhou 730000, China
E-mail: wangrui@lzu.edu.cn
Fax: (+86)-931-891-1255

b State Key Laboratory of Chiroscience and Department of Applied Biology & Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong
E-mail: bcrwang@polyu.edu.hk

Abstract

The first organocatalytic double Michael cascade reaction between unsaturated ketones and unsaturated pyrazolones has been developed which provides spiropyrazolone core structures containing two interval or three consecutive stereogenic centers with excellent diastereo- (>20 : 1) and enantioselectivities (up to 99% ee). Moreover, a pair of enantiomers 5 and 5′ can be achieved via different catalysts.

Graphical abstract: An organocatalytic asymmetric double Michael cascade reaction of unsaturated ketones and unsaturated pyrazolones: highly efficient synthesis of spiropyrazolone derivatives

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Article information

DOI
https://doi.org/10.1039/C2OB27095A
Article type
Communication
Submitted
27 Oct 2012
Accepted
10 Dec 2012
First published
11 Dec 2012

Org. Biomol. Chem., 2013,11, 1441-1445

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An organocatalytic asymmetric double Michael cascade reaction of unsaturated ketones and unsaturated pyrazolones: highly efficient synthesis of spiropyrazolone derivatives

J. Liang, Q. Chen, L. Liu, X. Jiang and R. Wang, Org. Biomol. Chem., 2013, 11, 1441 DOI: 10.1039/C2OB27095A

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