Examples of compounds displaying the tertiary amine–carbonyl interaction

March 11, 2024

• Title:       

   Examples of compounds displaying the tertiary amine–carbonyl interaction

• Image Source:

  Towards a biomimetic poly-aminoketone foldamer: synthesis of a triply protected monomer and its coupling to a dimer, trimer and tetramer

• Mark:

  Figure 1

• Associated context:

  The ^d+N/C]O^dꢀ interaction has been observed for nearly 80 years in a class of alkaloids (Fig. 1, 1) and in artificially made derivatives thereof. Researchers in the 1950s have performed solution-phase studies on these interactions in tropane derivatives (Fig. 1, 2), before they served as objects for the estimation of collision trajectories in nucleophilic attack on carbonyl groups by way of X-ray structure analysis in the 1970s.Later, sporadic occurrences in the synthetic literature (Fig. 1, 3 and 4)¹³ proved that these interactions were by no means limited to alkaloid systems. More recently we demonstrated that the ^d+N/C]O^dꢀ interaction can be incorporated into a peptidomimetic aimed to inhibit a particular protease.