Bertonazzi, Joanne
(2015)
Catalytic Asymmetric Construction of β-Amino Acid Precursors and Their Use in an Iterative Method Towards β-Peptide Synthesis.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
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.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
|
| Date: |
17 June 2015 |
| Date Type: |
Publication |
| Defense Date: |
26 March 2015 |
| Approval Date: |
17 June 2015 |
| Submission Date: |
3 April 2015 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| Number of Pages: |
107 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
PhD - Doctor of Philosophy |
| Thesis Type: |
Doctoral Dissertation |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
synthesis, β-peptides, thiazinone, peptidomimetics, organic chemistry, β-amino acid |
| Date Deposited: |
17 Jun 2015 14:07 |
| Last Modified: |
19 Dec 2016 14:42 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/24378 |
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