Synthesis of chi̇ral li̇gands and applications in catalytic reactions

In this master thesis, chiral derivatives of hydrobenzoin, containing bromine or phenyl ring, were synthesized and the electronic and steric effects of these synthesized chiral compounds were investigated in the catalytic reactions. Synthesized optically pure, compounds, (1R,2R)-1,2-bis (4'bromophenyl)-ethane-1,2-diol (4) and (1R,2R) -1,2-bis- (3'-phenylphenyl)-ethane-1,2-diol (5), are illuminated by using 1H-NMR, 13C-NMR, IR and mass analysis. Catalytic effects of synthesized chiral compounds, (4) and (5), was investigated in the enantioselective addition of diethylzinc to aldehydes. Compound (4) was used as ligand in the addition of ethyl to the 2-MeO benzaldehyde (%88 ee), compound (5) was also used as ligant (%85 ee). The synthesized compounds were tested as ligands in combination with titaniumtetraisopropoxide in the diethylzinc addition reactions with aldehydes and generally showed increased catalytic activity.