SATURATED NITROGEN-CONTAINING HETEROCYCLES. 14. SYNTHESIS AND THREE-DIMENSIONAL STRUCTURES OF N-R-DICYCLOPENTAPIPERIDINES

Article abstract of DOI:10.1007/BF00479347

The catalytic hydroamination of threo-methylenedicyclopentanone using ammonia, methylamine, and monoethanolamine as the aminating agents proceeds stereospecifically with the formation of N-R-cis-syn-cis-dicyclopentapiperidines (R=H, CH3, CH2CH2OH).The structures of the latter were proved by 13C NMR spectroscopy.The molecular structure of N-(β-hydroxyethyl)cis-syn-cis-dicyclopentapiperidinium acid tartrate was investigated by x-ray diffraction analysis, and the absolute configuration of its chiral centers was determined.