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 any organic cosolvent.
Department of Chemistry and Pharmacy, Institute of Organic Chemistry 1, University of Erlangen-Nuremberg, Henkestrasse 42, 91054, Erlangen, Germany.
Matthias
M
Freund
Sebastian
S
Schenker
Svetlana B
SB
Tsogoeva
D002384:Catalysis; D007659:Ketones / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry*; D011392:Proline; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry; D013379:Substrate Specificity; D014867:Water / Q000737:chemistry*
D007659:Ketones; D009842:Oligopeptides; D014867:Water; D020058:Styrene; D011392:Proline