Work

A Peptide-Embedded Trifluoromethyl Ketone Catalyst for Enantioselective Epoxidation

Year: 2012

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol3000712

Authors: David K. Romney, Scott J. Miller

Institution: Yale University

Language: English

Topic: Asymmetric Synthesis and Catalysis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: G1158090543, Selective Peptide-Based Oxidation Catalysts for Bioactive Molecule Synthesis