Issue 20, 2009
From the journal:

Organic & Biomolecular Chemistry

Enantioselective nitro-Michael reactions catalyzed by short peptides on water†

Matthias Freund,a   Sebastian Schenkera  and  Svetlana B. Tsogoeva*a  

* Corresponding authors

a Department of Chemistry and Pharmacy, Institute of Organic Chemistry 1, University of Erlangen-Nuremberg, Henkestrasse 42, Erlangen, Germany
E-mail: tsogoeva@chemie.uni-erlangen.de
Fax: +49-9131-85-26865
Tel: +49-9131-85-22541

Abstract

Simple unmodified N-proline-based di- and tripeptides in combination with sodium hydroxide additive catalyze the asymmetric Michael reaction of ketones with nitroolefins to furnish the corresponding γ-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent.

Graphical abstract: Enantioselective nitro-Michael reactions catalyzed by short peptides on water

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Article information

DOI
https://doi.org/10.1039/B910249C
Article type
Paper
Submitted
26 May 2009
Accepted
17 Jul 2009
First published
14 Aug 2009

Org. Biomol. Chem., 2009,7, 4279-4284

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Enantioselective nitro-Michael reactions catalyzed by short peptides on water

M. Freund, S. Schenker and S. B. Tsogoeva, Org. Biomol. Chem., 2009, 7, 4279 DOI: 10.1039/B910249C

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