同一の不斉源から両鏡像体を高光学純度で得る手法 : 触媒的不斉炭素-炭素結合形成反応を中心に  [in Japanese] New Approach for Complete Reversal of Enantioselection Using Schiff Base Ligand  [in Japanese]

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Author(s)

Abstract

Attempt for obtaining both enantiomers in high enantiomeric excess is attractive and important challenges, because it is often the case that each enantiomer exhibits different bioactivity. Since our first report on the chiral Schiff base-Ti (O-<I>i</I>-Pr) <SUB>4</SUB>-catalyzed trimethylsilylcyanation of aldehydes in 1991 (Aldimine type; the 1 st generation), this catalyst system has been proven to be efficient in a variety of asymmetric reactions. One of such reactions is the enantioselective addition of diketene to aldehydes. We succeeded in obtaining optically active 5-hydroxy-3-ketoesters in high optical yield (Ketimine type; the 2 nd generation). Herein, we report the first example of complete reversal of enantioselection using oxazoline-containing Schiff bases derived from <SUB>L</SUB>-serine, that is, from one stereogenic center of <SUB>L</SUB>-serine, both enantiomers of 5-hydroxy-3-keto-esters were obtained in high enantiomeric excess (Oxazoline containing type; the 3 rd generation).

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 65(10), 969-976, 2007-10-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10019836299
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    8972121
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  NDL  J-STAGE 
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