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Org Lett. 2012 Feb 17;14(4):1138-41. doi: 10.1021/ol3000712. Epub 2012 Feb 8.

A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.

Author information

1
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520, USA.

Abstract

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.

PMID:
22315978
PMCID:
PMC3288446
DOI:
10.1021/ol3000712
[Indexed for MEDLINE]
Free PMC Article

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