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A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.

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.

SUBMITTER: Romney DK

PROVIDER: S-EPMC3288446 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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A peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation.

Romney David K DK Miller Scott J SJ

Organic letters 20120208 4

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. ...[more]

PMID: 22315978

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