Peptide-Catalyzed Asymmetric Baylis-Hillman Reaction

Boston College, Chestnut Hill MA

Investigators

Abstract

DESCRIPTION (provided by applicant): The research proposal proposed herein describes the development of imidazole-functionalized peptides as catalysts: for the asymmetric Baylis-Hillman reaction. The results of such investigations will be the application of such C-C bond forming methods in a diversity-oriented synthesis toward multifunctional complex macrocycles. Specifically, we will be incorporating imidazole functionalized amino acids into peptides that have a propensity to form well defined conformations. We will proceed to screen the peptides for enantioselective catalytic activity in the Baylis-Hillman reaction. The result will be the development of a general catalytic method toward generating hydroxy-enones with complete stereocontrol. With an interest in applying the asymmetric Baylis-Hillman reaction in diversity-oriented synthesis, we will utilize the multifunctional nature of the hydroxy-enone to build a diverse library of stereochemically and structurally complex molecules.