Synthesis of chiral water-soluble metalloporphyrins (Fe, Ru,): new catalysts for asymmetric carbene transfer in water

The reaction of optically active Halterman porphyrin with sulfuric acid (95%) provided the expected water-soluble para-tetrasulfonated porphyrin in 82% yield. The metalloporphyrin complexes were prepared by metal insertion (iron) or direct sulfonation of the chiral ruthenium porphyrin. The asymmetric addition of diazoacetate to styrene to give optically active trans cyclopropyl ester (ee up to 86%) was carried out in water by using chiral iron or ruthenium porphyrins with a possible reuse due to the high solubility and stability in aqueous solution.