Chiral recognition of amines and amino acid derivatives by optically active ruthenium Halterman porphyrins in organic solvents and water

BODIPY- and Porphyrin-Based Sensors for Recognition of Amino Acids and Their Derivatives

“…Chiral recognition of nonpolar amino acids by ruthenium Halterman porphyrins in chloroform, methanol and water was reported by Nicolas et al [ 68 ]. In this study, a rigid porphyrin sensor 62 with Ru(CO) centre was employed to investigate ligation of the metal centre in trans position to the other axial ligand ( Figure 20 ).…”

Metalloporphyrin Symmetry in Chiral Recognition and Enantioselective Catalysis

“…In an attempt to obtain further information with regards to the existence of noncovalent interactions between amino acid side chains and the porphyrin ligand, we prepared a series of amine and amino ester complexes with C 4 -symmetric ruthenium(II) porphyrins [18]. Ruthenium(II) porphyrins form stable complexes with amine ligands [19].…”

“…For all ligands, except the phenylalanine methyl ester, the (S)-enantiomer was preferably ligated. The chiral recognition varied from 13% to 60% of enantiomeric excess (ee) [18]. The introduction of polar functional groups into the porphyrin was used to modify the solubility, as shown for the sulfonated porphyrins, with improved solubility in water.…”

“…We also described recent chiral epoxidation of alkenes in water/methanol solutions using H 2 O 2 as an oxidant catalyzed by new optically active water-soluble iron [43] and manganese porphyrins [44] (Figure 5). A chiral water-soluble Halterman porphyrin, due to the presence of four sulfonate groups at the para-position, was previously reported by our group and used for the chiral recognition of amino acids [18] and catalytic carbene transfer in water [45]. The starting point of the work described here was the introduction of four sulfonate groups into an optically active porphyrin with the aim of preparing water soluble porphyrins.…”

First enantioselective iron-porphyrin-catalyzed sulfide oxidation with aqueous hydrogen peroxide

“…A chiral water-soluble iron Halterman porphyrin, due to the presence of four sulfonate groups at the para-position, was previously reported by our group and used for chiral recognition of amino acids 27 and catalytic carbene transfer in water. 28 Herein we report its use for catalytic asymmetric sulfoxidation in polar solvents (water or methanol) by 35% aqueous hydrogen peroxide (Scheme 1).…”