Function-oriented investigations of a peptide-based catalyst that mediates enantioselective allylic alcohol epoxidation

We detail an investigation of a peptide-based catalyst (6) that is effective for the site- (>100 : 1 : 1) and enantioselective epoxidation (86% ee) of farnesol. Studies of the substrate scope exhibited by the catalyst are included, along with an exploration of optimized reaction conditions. Mechanistic studies are reported, including relative rate determinations for the catalyst and propionic acid, a historical perspective, truncation studies, and modeling using NMR data. Our compiled data advances our understanding of the inner workings of a catalyst that was identified through combinatorial means.