Synthetic Route of 51805-45-9, Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. 51805-45-9, Name is 3,3′,3”-Phosphinetriyltripropanoic acid hydrochloride, SMILES is Cl[H].OC(=O)CCP(CCC(O)=O)CCC(O)=O, belongs to chiral-phosphine-ligands compound. In a article, author is Popp, John, introduce new discover of the category.
Unusual Racemization of Tertiary P-Chiral Ferrocenyl Phosphines
Tertiary phosphines are generally known to withstand inversion under moderate conditions. In this work, a remarkable racemization process of three P-chiral ferrocenyl phosphines is reported. Subjected to conventional column chromatography as highly enantioenriched compounds, they greatly experienced racemization when collected at the column outlet within minutes. Initially, attention was drawn to this unusual inversion behavior after observing that the superb enantiomeric excess of these ligands (>95 % ee in all cases) was almost lost in their corresponding ruthenium(II) complexes. Successively excluding possible racemization causes, these P-chiral ferrocenyl phosphines were found to undergo a significant, acid-catalyzed racemization process at room temperature within a few minutes. This process is mainly observed during standard column chromatography by using conventional silica or alumina, but can also be triggered deliberately by addition of certain acids. Therefore, the stereochemical preservation of P-chiral phosphines during their purification may per se not always be guaranteed, since column chromatography is the most frequently used technique for purifying such types of compounds.
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Reference:
Phosphine ligand,
,Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate