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Issue 20, 2009

Enantioselective nitro-Michael reactions catalyzed by short peptides on water

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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

Supplementary files

Article information


Submitted
26 May 2009
Accepted
17 Jul 2009
First published
14 Aug 2009

Org. Biomol. Chem., 2009,7, 4279-4284
Article type
Paper

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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