高配位シリカートを経由する不斉Lewis塩基触媒反応  [in Japanese] Chiral Lewis Base-Catalyed Reactions Involving Hypervalent Silicates  [in Japanese]

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Author(s)

Abstract

Enantioselective reactions involving hypervalent silicate generated from trichlorosilane derivatives in the presence of chiral Lewis bases as catalysts are reviewed. Highly diastereo- and enantioselective allylations of aromatic and conjugate aldehydes with allyltrichlorosilanes have been developed by using chiral hexamethylphosphoramide (HMPA) derivatives or chiral bipyridine <I>N</I>, <I>N</I>' -dioxide derivatives as catalysts. Enantioselective allylations of aliphatic aldehydes have been accomplished by using chiral dimethylformamide (DMF) derivatives. It is strongly suggested that the present allylations proceed <I>via</I> cyclic chair-like transition structures involving hypervalent silicates. Enantioselective aldol reactions of aldehyde with trichlorosilyl enol ethers have been achieved by using chiral HMPA derivatives, which have been also effective in enantioselective ring opening of epoxides with tetrachlorosilane.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(9), 839-847, 2000-09-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008821576
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    Journal Article
  • ISSN
    00379980
  • NDL Article ID
    5474733
  • 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  CJPref  NDL  J-STAGE 
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