915781-01-0

The direct separation of the enantiomers of 1-(α-aminoarylmethyl)-2- naphthol, 1-(α-aminoalkyl)-2-naphthol, 2-(α-aminoarylmethyl)-1- naphthol analogs, and 2-(1-amino-2-methylpropyl)-1-naphthol) was performed on a newly developed chiral stationary phase containing isopropyl carbamate-cyclofructan6 as chiral selector, with n-heptane/alcohol/ trifluoroacetic acid as mobile phase. The effects of the mobile-phase composition, the nature and concentration of the alcoholic and acidic modifiers, and the structures of the analytes on the retention and resolution were investigated. In some cases, separations were carried out at constant mobile-phase compositions in the temperature range 5-40°C. Thermodynamic parameters and Tiso values were calculated from plots of ln k′ or ln α versus 1/T. -Δ(ΔH°) ranged from 2.8 to 3.2 kJ mol-1, -Δ(ΔS°) from 7.7 to 10.1 J mol-1 K-1, and -Δ(ΔG°) from 0.2 to 0.5 kJ mol-1. It was found that the enantioseparations were enthalpy driven. The sequence of elution of the stereoisomers determined in some cases was (R) (S).

New 1-(1-aminoalkyl)-2-naphthols 8-11 have been synthesised by the condensation of 2-naphthol with aliphatic aldehydes in the presence of ammonia, followed by acidic hydrolysis. The condensation of 7-11 with substituted benzaldehydes after microwave irrad