%0 Generic
%9 Doctoral Dissertation
%A Bertonazzi, Joanne
%D 2015
%F pittir:24378
%K synthesis, β-peptides, thiazinone, peptidomimetics, organic chemistry, β-amino acid  
%T Catalytic Asymmetric Construction of β-Amino Acid Precursors and Their Use in an Iterative Method Towards β-Peptide Synthesis 
%U http://d-scholarship-dev.library.pitt.edu/24378/
%X Towards the goal of novel β-peptide synthesis, a method to access a variety of enantioenriched β-amino acid precursors was developed.  These β-amino acid precursors were then utilized in the synthesis of numerous β-peptides in solution and on solid support.  The β-amino acid precursors allowing this unique technology are thiazinone and β-lactam heterocycles which were accessed via asymmetric cycloadditions of N-acyl imines and ketenes utilizing cinchona alkaloid catalysts.  The methodology developed herein provides access to unique and previously unavailable β-amino acids and β-peptides.