Catalytic Asymmetric Construction of β-Amino Acid Precursors and Their Use in an Iterative Method Towards β-Peptide Synthesis
Institution: | University of Pittsburgh |
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Department: | |
Year: | 2015 |
Posted: | 02/05/2017 |
Record ID: | 2134946 |
Full text PDF: | http://d-scholarship.pitt.edu/24378/7/ETD_JOANNE_BERTONAZZI_2015.pdf |
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.