Issue 20, 2011
From the journal:

Organic & Biomolecular Chemistry

Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study†

Zhiping Zeng,a   Ping Luo,a   Yao Jiang,a   Yan Liu,a   Guo Tang,a   Pengxiang Xu,a   Yufen Zhao*ab  and  G. Michael Blackburn*c  

* Corresponding authors

a Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, P. R. China
E-mail: yfzhao@xmu.edu.cn
Fax: +8605922185780
Tel: +8605922185780

b The Key Laboratory for Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, School of Sciences, Tsinghua University, Beijing, P. R. China

c Krebs Institute, Department of Molecular Biology & Biotechnology, Sheffield University, UK
E-mail: g.m.blackburn@sheffield.ac.uk
Fax: +44 114 2222800
Tel: +44 114 2229462

Abstract

A novel pyrrolidine-based chiral phosphoproline is an effective bifunctional organocatalyst for the asymmetric Michael addition of ketones to nitroolefins giving high levels of diastereo- and enantio-selectivities (up to > 99 : 1 dr and 96% ee). anti-SR Transition state has the lowest barrier which controls the stereoselectivity, in agreement with experimental results.

Graphical abstract: Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study

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Article information

DOI
https://doi.org/10.1039/C1OB06143G
Article type
Paper
Submitted
11 Jul 2011
Accepted
22 Jul 2011
First published
22 Jul 2011

Org. Biomol. Chem., 2011,9, 6973-6978

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Chiral phosphoproline-catalyzed asymmetric Michael addition of ketones to nitroolefins: an experimental and theoretical study

Z. Zeng, P. Luo, Y. Jiang, Y. Liu, G. Tang, P. Xu, Y. Zhao and G. M. Blackburn, Org. Biomol. Chem., 2011, 9, 6973 DOI: 10.1039/C1OB06143G

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