Asymmetric reductive amination of cycloalkanones, XIII: Enantioselective amidoamination: A new regiospecific strategy for the synthesis of chiral cyclohexane-1,2-diamino-derivatives

Article abstract of DOI:10.1002/ardp.19933260711

Asymmetric synthesis of trans- and cis-2-Benzamido- or 2-Phenyl-acetamido-cyclohexane-amines 7 and 8 by means of reductive amination and hydrogenolysis is described. Condensation of the amido-ketones 3 with chiral auxiliary (R)-(+) and (S)-(-)-1-phenylethylamine, respectively, leads to the amido-imines 4, which are hydrogenated over Raney-Ni to yield simultaneously enantiomerically pure secondary trans- and cis-2-amido-cyclohexane-amines 5 and 6.