ヒドロキシアルキルホスホニウム塩を用いたオキサホスホランの合成と反応  [in Japanese] Synthesis and Reaction of Oxaphospholanes by Using Hydroxyalkyl-phosphonium Salts  [in Japanese]

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Abstract

Triphenylvinylphosphonium salts were prepared by the reaction of triphenylphosphine with epoxide and acid, followed by the addition of acetyl chloride in one pot operation. These salts were also synthesized by the reaction of 2-hydroxyalkyltriphenylphosphonium salts with acetyl chloride or oxalyl chloride. Other synthetic methods of these salts were also described. Optically active 3-hydroxyalkyl triphenyl phosphonium salts were synthesized by the reaction of phospho-rus ylides with epoxides. The reaction of these salts with 2 eq of BuLi gave the corresponding γ-oxidephosphonium ylides, which further reacted with aldehydes to give the corresponding <I>E</I>-rich homoallylic alcohols. 2, 2, 2-Tripheny1-1, 2λ<SUP>5</SUP>-oxaphospholanes were easily prepared by the reaction of 3-hydroxylalkylphosphonium salts with sodium hydride. The reaction with aldehydes afforded <I>Z</I>-rich homoallylic alcohols almost quantitatively. Thus, high selectivity for <I>Z</I>- or <I>E</I>-homoallylic alcohols was available depending on the particular circumstances. The syntheses of optically active methylenecyclopropylacetic acid and recifeiolide were succeeded by this method.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(6), 548-555, 2000-06-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008820206
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    REV
  • ISSN
    00379980
  • NDL Article ID
    5365254
  • 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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