Asymmetric Lactone Synthesis via Hydroacylation and Stereoselective Cyclic Peptide Synthesis via Hydrogenation

Asymmetric transition metal catalysis has benefited human health by greatly facilitating access to natural products and therapeutic drugs. However, scientists continue to face challenges of developing more direct processes while minimizing the generation of unwanted wastes. As there is a high demand in the development of sustainable and atom-economical processes, the focus of my doctoral studies was to apply asymmetric catalysis in the development of conceptually unique and sustainable strategies for the synthesis of biologically important organic molecules. This dissertation includes: 1) the development of Rh-catalyzed enantioselective ketone hydroacylation as an atom-economical and general method for the synthesis of phthalide, 2) nickel catalyzed olefin hydroesterification for the synthesis of all-carbon quaternary stereocenters, and 3) a new synthetic strategy for preparing cyclic peptides using asymmetric hydrogenation.