CCB Colloquium presentation by Professor Jeffrey Johnston, Vanderbilt University.
Host: Daniel Seidel
Title: Reagent and Reaction Development in the Service of Complex Target Synthesis: Chiral Proton Catalysis, Umpolung Amide Synthesis, and Case Studies in Therapeutic Development
Abstract: Our discovery that chiral nonracemic Bis(AMidine) – ‘BAM’ – ligands can be effective modifiers of achiral Brønsted acids such as triflic acid became the basis for a general approach to fully stereocontrolled aza-Henry reactions. These reagents are bifunctional catalysts that rely on the basic principles of Brønsted acid (hydrogen bond) and base activation much like biological catalysts. Our latest findings in bifunctional Brønsted acid/Brønsted base catalyst design and development, reaction exploration, and target acquisition using these tools will be described. Our work to leverage chiral proton catalysis against the goal of fully enantioselective and efficient peptide synthesis via Umpolung Amide Synthesis (UmAS) will be introduced.
Davis, T. A.; Johnston, J. N. Chemical Science 2011, 2, 1076.
Chandra, A.; Johnston, J. N. Angew. Chem. Int. Ed. 2011, 50, 7641.
Shen, B.; Makley, D. M.; Johnston, J. N. Nature 2010, 465, 1027.