PM3 Analysis of Nitrone Cycloadditions to Methyl 4,4,4-Trifluoro-2-butenoate

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Abstract

3,4-Dihydroisoquinoline <i>N</i>-oxide (<b>1</b>) cycloadded with methyl 4,4,4-trifluoro-2-butenoate at 20 °C to give a mixture of the cycloadduct with a 1,10b-<i>cis</i>-configuration, methyl (1<i>R</i><sup>*</sup>, 2<i>R</i><sup>*</sup>, 10b<i>R</i><sup>*</sup>)-2-trifluoromethyl-1,5,6,10b-tetrahydro-2 <i>H</i>-isoxazolo[3,2-<i>a</i>]isoquinoline-1-carboxylate, and its stereoisomer with a 1,10b-<i>trans</i>-configuration in a ratio of 3 : 1. Nitrone <b>1</b> cycloadded with methyl 2-butenoate to afford the cycloadduct with a 1,10b-<i>cis</i>-configuration exclusively. The stereoselectivity in the cycloadditions was reproduced by calculations of the transition structures by the PM3 method.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 69(8), 2243-2248, 1996-08-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008907155
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • NDL Article ID
    4060543
  • 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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