Asymmetric Synthesis of the Both Enantiomers of α-Hydroxy Acids by the Diastereoselective Reduction of Chiral α-Keto Amides with (Complex) Metal Hydrides in the Presence of Metallic Salt

DOI DOI PDF 参考文献10件
  • Soai Kenso
    Department of Applied Chemistry, Faculty of Science, Science University of Tokyo
  • Isoda Takeshi
    Department of Applied Chemistry, Faculty of Science, Science University of Tokyo
  • Hasegawa Hitoshi
    Department of Applied Chemistry, Faculty of Science, Science University of Tokyo
  • Ishizaki Miyuki
    Department of Applied Chemistry, Faculty of Science, Science University of Tokyo

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説明

Effects of the metallic salts and the reducing reagents in the diastereoselective reduction of chiral α-keto amides derived from (S)-proline methyl ester were examined. Lithium borohydride afforded (S)-α-hydroxy acids, whereas diisobutylaluminum hydride afforded (R)-isomers. In the presence of lithium bromide, reduction with LiBH4 afforded (S)-mandelic acid in over 80% e.e.

収録刊行物

  • Chemistry Letters

    Chemistry Letters 15 (11), 1897-1900, 1986-11-05

    公益社団法人 日本化学会

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