Ruthenium complexes, prepared by mixing the potassium salt of a-amino acids and [RuCl 2 (arene)] 2 , acted as catalysts for the asymmetric transfer hydrogenation of ketones from 2-propanol in the presence of KOH. For example, the transfer hydrogenation of acetophenone from 2-propanol was catalyzed effectively by the ruthenium complex prepared from potassium L-prolinate and [RuCl 2 (p-cymene)] 2 to give (R)-1-phenylethanol in 72% yield with 81% ee. The yields and enantioselectivities of the product were influenced strongly by the structure of the a-amino acidate ligand, arene ligand, and substrate, by the amount of additional base, and by the concentration of the substrates. The best enantiomeric excesses of the products was 92%, when 1-tetralone was subjected to this reaction using a prolinated ruthenium complex bearing p-cymene. Furthermore, the potassium salts of dipeptides were tested as a ligand for this transfer hydrogenation.
Ruthenium complexes, prepared by mixing potassium salt of α-amino acids and [RuCl2(arene)]2, acted as catalysts for asymmetric transfer hydrogenation of ketones from 2-propanol in the presence of KOH, and enantiomeric excesses of the products reached 92%.
stereochemistry stereochemistry (general, optical resolution) O 0030 44 -041 α-Amino Acidate-Ru(II) Catalysts for Asymmetric Transfer Hydrogenation: First Utilization of α-Amino Acids as an Efficient Ligand. -Ru-complexes (I) derived from potassium salts of α-amino acids and Ru 2 Cl 4 (arene) 2 prove to be efficient catalysts for the asymmetric transfer hydrogenation of ketones from alcohols. Enantiomeric excesses of the products reach 92%. -(OHTA, T.; NAKAHARA, S.; SHIGEMURA, Y.; HATTORI, K.; FURUKAWA, I.; Chem. Lett. (1998) 6, 491-492; Dep. Mol. Sci. Technol., Fac. Eng., Doshisha Univ., Tanabe, Kyoto 610-03, Japan; EN)
diastereoselective syntheses, enantioselective syntheses diastereoselective syntheses, enantioselective syntheses (incl. cis/trans-isomerism) O 0031
-027α-Amino Acid: An Effective Ligand for Asymmetric Catalysis of Transfer Hydrogenation of Ketones.-19 Amino acids and 16 dipeptides are tested as ligands for asymmetric transfer hydrogenation of prochiral ketones. The corresponding ruthenium catalysts are prepared from [RuCl 2 (p-cymene)] 2 and the potassium salt of the amino acid or dipeptide, respectively. Best results are obtained using proline-derived catalyst RCPC (cf. scheme). This reaction is lauded to provide the first efficient asymmetric catalytic method directly using an α-amino acid as a ligand.-(OHTA,
Bei der katalytischen Hydrogenierung an Pd‐Kohle der Titelverbindung (I) entsteht neben den Aminen (IIIa)‐(IIIc) das neuartige tricyclische Lactam (II).
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.