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

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2011
Günler, Zeynep İnci
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.
Citation Formats
Z. İ. Günler, “Synthesis of n-(2-propylphenyl) substituted chiral amino alcohols and their usage in enantioselective diethylzinc addition reactions,” M.S. - Master of Science, Middle East Technical University, 2011.