Stereoselective Synthesis of trans-2, 5-Disubstituted Tetrahydrofurans via the Lewis Acid Mediated Reduction of Cyclic Hemiketals with Triphenylsilane

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著者

    • NISHIYAMA Yutaka
    • Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai University
    • TUJINO Takashi
    • Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai University
    • YAMANO Tadamichi
    • Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai University
    • ITOH Kazuyoshi
    • Department of Applied Chemistry, Faculty of Engineering and HRC, Kansai University

抄録

An efficient method for the synthesis of <I>trans</I>-2,5-disubstituted tetrahydrofuran derivatives has been developed. Dithioacetal-functionalized cyclic hemiketals are reduced by triphenylsilane (Ph<SUB>3</SUB>SiH) in the presence of TiCl<SUB>4</SUB> to afford the corresponding <I>trans</I>-2,5-disubstituted tetrahydrofuran derivatives in good yield and high stereoselectivity. Asymmetrical synthesis of (2<I>S</I>,5<I>S</I>) disubstituted tetrahydrofuran was also achieved by using this reduction method.

収録刊行物

  • Chemistry letters

    Chemistry letters 1997(2), 165-166, 1997-02

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10002609864
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    03667022
  • データ提供元
    CJP書誌  CJP引用  J-STAGE 
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