Function-Oriented Investigations of a Peptide-Based Catalyst that Mediates Enantioselective Allylic Alcohol Epoxidation.
We detail an investigation of a peptide-based catalyst6that 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.
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.
Nadia C
NC
Abascal
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.
Phillip A
PA
Lichtor
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.
Michael W
MW
Giuliano
Department of Chemistry, Yale University, P.O. Box 208107, New Haven, Connecticut 06520-8107, United States.
Scott J
SJ
Miller