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1	Synthesis of Heterocyclic Chiral Diamines and Use of Diamine-based Chiral Guanidines to Determine Enantiopurity of Amino Acids Mui, Leo 12 January 2011 (has links) 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. chemistry organic amino acid optical purity enantiomer stereoselective diamine vicinal diamine chiral diamine synthesis heterocycle guanidine chiral shift reagent NMR 0490 0487
2	Synthesis of Heterocyclic Chiral Diamines and Use of Diamine-based Chiral Guanidines to Determine Enantiopurity of Amino Acids Mui, Leo 12 January 2011 (has links) 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. chemistry organic amino acid optical purity enantiomer stereoselective diamine vicinal diamine chiral diamine synthesis heterocycle guanidine chiral shift reagent NMR 0490 0487

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Synthesis of Heterocyclic Chiral Diamines and Use of Diamine-based Chiral Guanidines to Determine Enantiopurity of Amino Acids

Synthesis of Heterocyclic Chiral Diamines and Use of Diamine-based Chiral Guanidines to Determine Enantiopurity of Amino Acids