いかにしてフォトクロミック電子環状反応を立体選択的に行うか  [in Japanese] How to Conduct Photochromic Electrocyclization Stereoselectively  [in Japanese]

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Abstract

The development of highly diastereoselective photochromic compounds that our group has carried out in the past 15 years is described here. Observations by <SUP>1</SUP>H NMR of the enantiomeric isomerization of helically chiral hexatriene moiety of a fulgide which undergoes photochemical 6π-electrocyclization are first described, followed by discussions on the optical resolution of a fulgide and diastereoselective photochromism of an (<I>R</I>)-binaphthol-modified fulgide. A new concept of diastereoselective photochromism has also been realized by using diarylethenes as the template. The concept consists of: (i) Allylic 1,3-strain and (ii) electronic and steric repulsions between the oxygen atoms on a substituent on the stereogenic carbon atom attached to the ring-closing carbon atom located at one terminal of the hexatriene moiety and the heteroatom on the second heteroaromatic ring. Finally, a general strategy to achieve extraordinarily high diastereoselectivity of up to 100:0 has been demonstrated by the introduction of dual chiral stereocontrolling substituents to diarylethenes.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 68(1), 52-63, 2010-01-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10026867688
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    10558740
  • 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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