Issue 2, 2008
From the journal:

Organic & Biomolecular Chemistry

Highly enantioselective Michael addition of malononitrile to α,β-unsaturated ketones†

Xuefeng Li,ab   Lingfeng Cun,a   Chunxia Lian,a   Ling Zhong,a   Yingchun Chen,c   Jian Liao,a   Jin Zhua  and  Jingen Deng*a  

* Corresponding authors

a National Engineering Research Center of Chiral Drugs and Key Laboratory of Asymmetric Synthesis & Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, The Chinese Academy of Sciences, Chengdu 610041, China
E-mail: jgdeng@cioc.ac.cn
Fax: +86 28 8522 3978

b Graduate School of the Chinese Academy of Sciences, Beijing 100049, China

c West China School of Pharmacy, Sichuan University, Chengdu 610041, China

Abstract

The highly enantioselective Michael addition of malononitrile to acyclic and cyclic α,β-unsaturated ketones has been developed. The Michael reaction catalyzed by a primary amine derived from quinidine proceeded smoothly and provided the desired adducts with excellent enantioselectivities (83–97% ee).

Graphical abstract: Highly enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

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Article information

DOI
https://doi.org/10.1039/B713129A
Article type
Paper
Submitted
28 Aug 2007
Accepted
14 Nov 2007
First published
03 Dec 2007

Org. Biomol. Chem., 2008,6, 349-353

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Highly enantioselective Michael addition of malononitrile to α,β-unsaturated ketones

X. Li, L. Cun, C. Lian, L. Zhong, Y. Chen, J. Liao, J. Zhu and J. Deng, Org. Biomol. Chem., 2008, 6, 349 DOI: 10.1039/B713129A

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