A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, SDS of cas: 29841-69-8, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 29841-69-8, Name is (1S,2S)-(-)-1,2-Diphenylethylenediamine, molecular formula is C14H16N2. In a Conference Paper, authors is Gelalcha, Feyissa Gadissa,once mentioned of 29841-69-8
A novel and general biomimetic non-heme Fe-catalyzed asymmetric epoxidation of aromatic alkenes by using hydrogen peroxide is reported herein. The catalyst consists of ferric chloride hexahydrate (FeCl3·OH 2O), pyridine-2,6-dicarboxylic acid (H2-(pydic)), and readily accessible chiral N-arenesulfonyl-N?-benzyl-substituted ethylenediamine ligands. The asymmetric epoxidation of styrenes with this system gave high conversions but poor enantiomeric excesses (ee), whereas larger alkenes gave high conversions and ee values. For the epoxidation of trans-stilbene (1a), the ligands (S,S)-N-(4-toluenesulfonyl)-1,2- diphenylethylenediamine ((S,S)-4a) and its N?-benzylated derivative ((S,S)-5a) gave opposite enantiomers of trans-stilbene oxide, that is, (S,S)-2a and (R,R)-2a, respectively. The enantioselectivity of alkene epoxidation is controlled by steric and electronic factors, although steric effects are more dominant. Preliminary mechanistic studies suggest the in situ formation of several chiral Fe-complexes, such as [FeCl(L*)2-(pydic)] ·HCl (L* = (S,S)-4a or (S,S)-5a in the catalyst mixture), which were identified by ESIMS. A UV/Vis study of the catalyst mixture, which consisted of FeCl3·6H2O, H2(pydic), and (S,S)-4a, suggested the formation of a new species with an absorbance peak at lambda = 465 nm upon treatment with hydrogen peroxide. With the aid of two independent spin traps, we could confirm by EPR spectroscopy that the reaction proceeds via radical intermediates. Kinetic studies with deuterated styrenes showed inverse secondary kinetic isotope effects, with values of k H/kD = 0.93 for the beta carbon and kH/k D=0.97 for the a carbon, which suggested an unsymmetrical transition state with stepwise O transfer. Competitive epoxidation of para-substituted styrenes revealed a linear dual-parameter Hammett plot with a slope of 1.00. Under standard conditions, epoxidation of la in the presence of ten equivalents of H218O resulted in an absence of the isotopic label in (S,S)-2a. A positive non-linear effect was observed during the epoxidation of la in the presence of (S,S)-5a and (R,R)-5a.
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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI