Issue 20, 2011

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

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Jul 2011
Accepted
22 Jul 2011
First published
22 Jul 2011

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

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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