The chiral vicinal diamine moiety is “privileged” and is widely found in catalysts and bio-active compounds. A series of seven chiral vicinal diamines with heterocyclic substituents have been synthesized with great enantiospecificity via the resonance assisted hydrogen bond driven diaza-Cope rearrangement reaction using 1,2-bis(2-hydroxyphenyl)-1,2-diaminoethane and heterocyclic aldehydes as starting materials.
This thesis will also discuss the development of a new guanidine-based chiral shift rea-gent for determining the enantiopurity and the absolute configuration of α-amino acids by proton nuclear magnetic resonance (1H NMR) spectroscopy. The chiral shift reagent is easily synthesized from the commercially-available 1,2-diphenyl-1,2-diaminoethane. This method is advantageous over many previously described procedures for determining amino acid enantiopurity as it does not require prior derivatization of the analyte.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/25842 |
| Date | 12 January 2011 |
| Creators | Mui, Leo |
| Contributors | Chin, Jik |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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