Synthesis of n-(2-propylphenyl) substituted chiral amino alcohols and their usage in enantioselective diethylzinc addition reactions


Thesis Type: Postgraduate

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

Approval Date: 2011

Thesis Language: English

Student: Zeynep İnci Günler

Supervisor: CİHANGİR TANYELİ

Abstract:

IChiral 1,2-amino alcohols were synthesized via newly developed “intramolecular unsaturation transfer” using cyclohexanone, propargyl bromide, and various chiral amino alcohols as starting components. These amino alcohols can be potential chiral ligands for many asymmetric transformation reactions. Therefore, their effectiveness as chiral ligands in diethylzinc addition to benzaldehyde and N-diphenylphosphinoyl imines were tested. Various parameters including temperature, solvent, ligand amount etc. were screened for the synthesized chiral ligands. In diethylzinc addition to benzaldehyde high enantioselectivity could not be obtained. When N-diphenylphosphinoyl imines were used as substrate good ee values up to 80% were achieved.