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α‐Amino acid: an effective ligand for asymmetric catalysis of transfer hydrogenation of ketones
Authors:Tetsuo Ohta  Shu‐ichi Nakahara  Yasuhiko Shigemura  Kouichi Hattori  Isao Furukawa
Abstract:Ruthenium complexes, prepared by mixing the potassium salt of α‐amino acids and [RuCl2(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 [RuCl2(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 α‐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. Copyright © 2001 John Wiley & Sons, Ltd.
Keywords:α  ‐amino acid  asymmetric transfer hydrogenation  ruthenium catalyst  chiral alcohol  dipeptide
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