Synthesis of New C2-Symmetric Chiral Bisamides from (1S,2S)-Cyclohexane-1,2-dicarboxylic Acid

A series of new C-2-symmetric (1S,2S)-cyclohexane-1,2-dicarboxamides was synthesized from (1S,2S)-cyclohexane-1,2-dicarbonyl dichloride and N-benzyl-substituted aromatic amines, which were prepared from 2-aminopyridine, 2-chloroaniline, and 2-aminophenol via imine formation with benzaldehyde and subsequent reduction with NaBH4. (1S,2S)-N,N-Dibenzyl-N,N-bis[2-(benzyloxy)phenyl]cyclohexane-1,2-dicarboxamide was converted to (1S,2S)-N,N-dibenzyl-N,N-bis(2-hydroxyphenyl)cyclohexane-1,2-dicarboxamide via hydrogenolysis in the presence of Pd(OH)(2) on active carbon powder.