The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic, and theoretical assessments of solvent structures and their interactions with reaction intermediates and transition states. 526-95-4, Name is Gluconic Acid (contains Gluconolactone), SMILES is O[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)C(O)=O, in an article , author is Li, Wanfang, once mentioned of 526-95-4, Synthetic Route of 526-95-4.
A series of 3-oxoglutaric acid derivatives have been hydrogenated in different solvents in the presence of [RuCl(benzene)(S)-SunPhos]Cl (SunPhos=(2,2,2′,2′-tetramethyl-[4,4′-bibenzo[d][1,3]dioxole]-5,5′-diyl)bis(diphenylphosphine)). Unlike simple beta-keto acid derivatives, these advanced analogues can be readily hydrogenated in uncommon solvents such as THF, CH2Cl2, acetone, and dioxane with high enantioselectivities. Two possible catalytic cycles have been proposed to explain the different reactivities of these 1,3,5-tricarbonyl substrates in the tested solvents. The C-2 and C-4 substituents had notable but irregular influence on the reactivity and enantioselectivity of the reactions. More pronounced solvent effects were observed: the ee values increased from around 20?% in EtOH or THF to 90?% in acetone. Inversion of the product configuration was observed when the solvent was changed from EtOH to THF or acetone, and a mixed solvent system can lead to better enantioselectivity than a single solvent.
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Reference:
1,3-Benzodioxole – Wikipedia,
,Dioxole | C3H4O2 – PubChem