We have established that chiral nonracemic Bis(AMidine) � 'BAM' � ligands can be effective modifiers of achiral Br�nsted acids, such as triflic acid. The reagents that result are the basis for a general approach to fully stereocontrolled aza-Henry reactions, and more recently, enantioselective iodolactonization. These reagents are bifunctional catalysts that rely on the basic principles of Br�nsted acid (hydrogen bond) and base activation much like biological catalysts. This lecture will highlight an ongoing thrust to both streamline peptide synthesis and broaden the number of non-natural amino acids that can be easily installed during peptide homologation. Key to this goal is the development of Umpolung Amide Synthesis (UmAS). Our work to leverage the attributes of BAM�catalysis and UmAS against functionally and stereochemically dense targets will be shared. Our development of N-silyl imines as Rosetta stones for peptide synthesis will be highlighted.

Award Address  (Arthur C. Cope Mid Career Scholars Award sponsored by the Arthur C. Cope Fund). Reagent and reaction development in the service of complex target synthesis and therapeutic development

248th National Meeting (2014)

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