A Concise Ring Closing Enyne Metathesis Approach for the Preparation of Functionalized Proline‐Derived Azabicycloalkane Amino Acids

Herein we report the preparation of C4-functionalized proline-derived azabicycloalkane (Aba) amino acids by exploiting a direct ring closing enyne metathesis reaction of readily accessible dipeptide precursors. The reverse-turn inducing properties of the newly synthesized constrained dipeptide mimics were assessed by computational studies. Furthermore, the desired Aba derivatives, carrying a synthetically versatile diene moiety, were subjected to post-functionalization reactions to validate their potential application in peptide/peptidomimetic chemistry and drug discovery.Constrained C4-functionalized dipeptide derivatives incorporating a proline moiety were prepared in high yields by exploiting a direct ring closing enyne metathesis (RCEYM) reaction. Post-functionalization studies of the newly introduced diene system pave the way for future applications in peptide synthesis, medicinal chemistry and nanotechnology. image