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A study to demonstrate that the readily accessible 5,10-bis(2',6'-dibromophenyl)porphyrins are versatile synthons for modular construction of chiral porphyrins via palladium-catalyzed multiple amidation reactions with chiral amides is presented. Findings show that Cobalt(II) complexes of the D2-symmetric chiral prophyrins are active catalysts for highly enantioselective and diastereoselective cyclo-propanation under a practical one-pot protocol.

This article focuses on bromoporphyrins. Metalloporphyrins have been found to catalyze a range of fundamentally and practically important chemical transformations, some of which represent the first demonstrations of such catalytic processes. Due to the unique ligand environment and metal coordination mode, unusual reaction selectivities and excellent catalyst turnovers have been observed for metalloporphyrin-based catalysts. Although significant progress has been made, catalytic reactions based on metalloporphyrins have not been developed into practical methodologies that can be used in asymmetric synthesis.