Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration

Nitration of tetraphenylporphyrin cage compound 1, at −40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at −30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of 5:2, which were separated by chromatography (46 and 20% yields, respectively). The structures of the compounds were confirmed by X-ray crystallography.