(1S,7S)-7-Methyl-6,9-diazatricyclo[6,3,0,01,6]tridecane-5,10-dione, a tricyclic spirodilactam containing non-planar amide groups: Synthesis, NMR, crystal structure, absolute configuration, electronic and vibrational circular dichroism
The title spirocyclic dilactam (1S,7S)-7-methyl-6,9-diazatricyclo[6,3,0,01,6]tridecan-5,10-dione (I), a molecule designed to contain non-planar amide groups, has been synthesized from an optically active precursor of known absolute configuration. The relative and absolute configuration have been determined by X-ray diffraction. The conformation of the compound has been investigated by X-ray, 1H and 13C NMR, electronic and vibrational circular dichroism. The compound possesses moderately non-planar amide groups in the two rings of nonequal geometry. The electronic CD is dominated by inherent chirality of the amide chromophores. The dilactams I and II ((1S,6S)-6-methyl-5,8-diazatricyclo[6,3,0,01,5]undecan-4,9-dione – having five-membered rings) exhibit monosignate amide I VCD and strong VCD bands in the mid-ir region.