Regioselective Robinson Annula.tion Realized by the Combined Use of Lithium Enolates and Aluminum Tris(2,6-diphenylphenoxide) (ATPH)

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Abstract

Michael addition of lithium enolates derived from ketones to a variety of <i>α</i>,<i>β</i>-unsaturated ketones was realized in the presence of aluminum tris(2,6-diphenylphenoxide) (ATPH). In this reaction, ATPH can be used as a carbonyl protector of <i>α</i>,<i>β</i>-unsaturated carbonyl substrates upon complexation, which facilitates the regioselective 1,4-addition of lithium enolates to Michael acceptors. Similarly, dianions of <i>β</i>-dicarbonyl compounds undergo Michael addition smoothly using ATPH as an effective promoter of the reaction. Subsequent regioselective, intramolecular aldol condensation was also demonstrated, leading to bicyclic carbon ring systems. Such systems are difficult to obtain by the Robinson annulation usually performed in protic media.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(7), 1671-1681, 1997-07-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008920846
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4260307
  • NDL Source Classification
    ZP1(科学技術--化学・化学工業)
  • NDL Call No.
    Z53-B35
  • Data Source
    CJP  NDL  J-STAGE 
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