New enantiomerically pure aminoalcohols from (R)-alpha-methylbenzylamine and cyclohexene oxide

The new chiral aminoalcohols N-{(S)-[cyclohexan-(S)-2-ol]}-(R)-alpha-methylbenzyl amine 1 and N-{(R)-[cyclohexan-(R)-2-ol]}-(R)-alpha-methylamine 2 were prepared by reaction of (R)-alpha-methylbenzylamine with cyclohexene oxide at 160 degrees C. The diastereoisomers were separated by fractional crystallization of the corresponding ammonium chlorides N-{(S)-[cyclohexan-(S)-2-ol]}-(R)-alpha-methylbenzyl ammonium chloride 1 . HCl and N-{(R)-[cyclohexan-(R)-2-ol]}-(R)-alpha-methylbenzyl ammonium chloride 2 . HCl. The absolute configuration of all stereocenters in 1 . HCl and 2 . HCl was determined by X-ray diffraction analyses. (C) 1996 Elsevier Science Ltd