A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.
The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, USA.
David K
DK
Romney
Scott J
SJ
Miller
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry*; D017611:Fluorine Compounds / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D017611:Fluorine Compounds; D007659:Ketones; D010455:Peptides; D013141:Spiro Compounds