Development of an asymmetric conjugate addition of azide ion catalyzed by short folded peptides

Chapter 1. A brief overview on methods to access β-amino acid synthons utilizing enantioselective conjugate addition strategies is presented. Strategies employing chiral auxiliary-based and chiral nucleophile-based methods are described, as well as efforts relying on asymmetric catalysis are highlighted.; Chapter 2. An efficient, general-base catalyzed conjugate addition of azide ion to various α,β-unsaturated carbonyl compounds is described. Highlights include mild reaction conditions, clean reactions with high yields, and conversion of the azide products to β-amino acid derivatives.; Chapter 3. Development of a peptide-based, asymmetric conjugate addition of azide ion is described. Moderate to high enantioselectivities are obtained in the conjugate addition of several unsaturated imide substrates using simple tetrapeptide catalysts. Subsequent conversion of the azide products to optically enriched β-amino acids and triazoles is discussed as well.; Chapter 4. Efforts to apply the developed asymmetric conjugate addition protocol in target-oriented synthesis are discussed. Using the azidation protocol, efficient syntheses of mitomycin-like targets were realized.