Novel functionalized azaheterocycles with multiple chiral centers have been accessed from readily available norbornene β-amino acids or β-lactams across a stereocontrolled synthetic route, based on ring-opening metathesis (ROM) of the staring unsaturated bicyclic amino esters, followed by selective cyclization through ring-closing metathesis (RCM). The RCM transformations have been studied under various experimental conditions to assess the scope of conversion, catalyst, yield, and substrate influence. The structure of the starting norbornene β-amino acids predetermined the structure of the new azaheterocycles, and the developed synthetic route took place with the conservation of the configuration of the chiral centers.

The synthesis of some novel functionalized azaheterocyclic β‐amino esters with multiple chiral centers via a stereocontrolled synthetic route has been carried out using some cyclooctene β‐amino acids as starting model compounds. The strategy of the method was planned to create some novel unsaturated N‐protected cyclic β‐amino esters that were subjected to ring‐opening metathesis (ROM) followed by selective ring‐closing metathesis (RCM). A number of experimental conditions were accomplished to investigate the activity of catalysts, yields, conversions, and substrate effect on ring‐rearrangement metathesis (RRM) transformation. Importantly, the procedure used in this synthetic process does not affect the configuration of the chiral centers; therefore, the stereochemistry of the starting cyclooctadiene β‐amino acids predetermined the structure of the new azaheterocyclic derivatives.

The synthesis of some new functionalized azaheterocyclic β-amino esters with multiple stereocenters has been achieved from readily available unsaturated bicyclic β-amino acids via a stereocontrolled synthetic protocol, which utilized N-allylation/propargylation, ring-opening metathesis (ROM), and selective ring-closure with chemodifferentiation through ring-closing metathesis (RCM). The RCM transformations have been investigated under various experimental conditions to analyze the scope of catalyst, yield, conversion, and substrate effect. The structure of the starting (oxa)norbornene β-amino acids predetermined the structure of the new azaheterocyclic derivatives; the described synthetic procedure proceeded with the conservation of the configuration of the stereogenic centers.