Peptides are appealing scaffolds for asymmetric catalysis due to their inherent modularity and ease of synthesis.  Not only do these scaffolds provide a readily available chiral environment, but the selectivity of these catalysts can also be tuned by varying the sequence of amino acids.  By incorporating a highly electrophilic ketone into a short peptide sequence, we have been able to develop a catalyst capable of epoxidizing unfunctionalized alkenes in good yields and enantioselectivities.  The extension of this methodology to other oxidation reactions will be presented.

Peptide-embedded ketones as catalytic asymmetric oxidants

244th National Meeting (2012)

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