Development of novel asymmetric catalysts for various transformations and investigation of a rearrangement reaciıon

Thesis Type: Doctorate

Institution Of The Thesis: Middle East Technical University, Faculty of Arts and Sciences, Department of Chemistry, Turkey

Approval Date: 2010

Thesis Language: English

Student: Emre Yusuf Yazıcıoğlu



A new class of pyridine and sulfur containing chiral compounds are synthesized. Camphor sulfonyl chloride is chosen as a valuable chiral starting compound. In our synthetic strategy, sulfonylchloride moiety is first reduced to corresponding thiol compound by using triphenylphosphine and then the resultant thiol will be converted to various alkyl, aryl substituted derivatives. The second part of our strategy includes the pyridine ring construction on the carbonyl side of camphor with the formation of β-hydroxymethylene moiety followed by further reaction with various enamines. The resultant chiral ligands are characterized and used as a chiral ligand in asymmetric transfer of hydrogenation. Also novel class of organocatalysts synthesized from C2-symmetrical chiral diamine backbones and halopyridine derivatives are also synthesized and tested for their performance in kinetic resolution of racemic secondary alcohols. Also, a base mediated aromatization reaction is investigated in terms of both scope and mechanism.