Enantioselective nitro-Michael reactions catalyzed by short peptides on water

Enantioselective nitro-Michael reactions catalyzed by short peptides on water

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 gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without...

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Veröffentlicht in:Organic & biomolecular chemistry 2009-01, Vol.7 (20), p.4279-4284
Hauptverfasser: Freund, Matthias, Schenker, Sebastian, Tsogoeva, Svetlana B
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Ketones - chemistry
Oligopeptides - chemistry
Proline
Stereoisomerism
Styrene - chemistry
Substrate Specificity
Water - chemistry
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Zusammenfassung: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 gamma-nitroketones with up to 99% yield, 99:1 dr and 70% ee at room temperature and on water without any organic cosolvent.
ISSN:1477-0520
1477-0539
DOI:10.1039/b910249c