Selective Transformation of Norbornadiene into Functionalized Azaheterocycles and ß-Amino Esters with Stereo- and Regiocontrol.

ABSTRACT

Novel functionalized azaheterocycles with multiple chiral centers have been accessed from readily available norbornene ß-amino acids or ß-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 ß-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.