Issue 20, 2011
From the journal:

Chemical Communications

Asymmetric organocatalytic cascade Michael/hemiketalization/retro-Henry reaction of β,γ-unsaturated ketoesters with α-nitroketones†

Yaojun Gao,a   Qiao Ren,a   Woon-Yew Siaua  and  Jian Wang*a  

* Corresponding authors

a Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543
E-mail: chmwangj@nus.edu.sg
Fax: (+) 65-6516-1691

Abstract

An unprecedented enantioselective organocatalytic Michael/hemiketalization/retro-Henry cascade sequence is described, which catalyzed by a simple bifunctional indane amine-thiourea catalyst. This process provides a new route to the enantioselective synthesis of 5-nitro-pent-2-enoates, a precursor to α-ketolactam.

Graphical abstract: Asymmetric organocatalytic cascade Michael/hemiketalization/retro-Henry reaction of β,γ-unsaturated ketoesters with α-nitroketones

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Article information

DOI
https://doi.org/10.1039/C1CC11124H
Article type
Communication
Submitted
25 Feb 2011
Accepted
23 Mar 2011
First published
12 Apr 2011

Chem. Commun., 2011,47, 5819-5821

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Asymmetric organocatalytic cascade Michael/hemiketalization/retro-Henry reaction of β,γ-unsaturated ketoesters with α-nitroketones

Y. Gao, Q. Ren, W. Siau and J. Wang, Chem. Commun., 2011, 47, 5819 DOI: 10.1039/C1CC11124H

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