Synthesis and characterization of original N-meso chiral substituted diarylporphyrins

A first palladium catalyzed cross-coupling amination with chiral auxiliaries at the two meso positions of diarylporphyrins was reported. We noticed that, the non-metallation of porphyrins and steric hinderance of the chiral auxiliary play an essential role to the effectiveness of this cross coupling-reaction. Here, when two methyl pyroglutamates were added, the reaction leads to atropisomers and their behaviors were investigated by NMR spectroscopy. Finally, functionalizations of these chiral porphyrins were performed onto the pyrroglutamate moiety to give new original chiral porphyrins.