Effect of intramolecular interactions on circular dichroism of ortho-substituted 1-phenethylamines.

The synthesis of ortho-substituted (S)-1-phenethylamines via ortho-lithiation of its N,N-dimethyl derivative followed by reactions with different reagents is described. Circular dichroism spectra of synthesized compounds were measured. It is shown that the observed short-wave Cotton effects greatly depend on the existence of cyclic structure due to possible interactions such as hydrogen bond or electrostatic interaction.

Catalyzed asymmetric dialkylzinc addition to benzaldehyde in the presence of new chiral ligands--delta-(1-phenethyl)aminoalcohols.

A series of delta-aminoalcohols prepared from (S)- and (R)-N,N-dimethyl-1-phenethylamines was found to catalyze the enantioselective addition of diethylzinc to benzaldehyde to yield optically active 1-phenylpropanol with enantiomeric excess 60-85%.