High 1, 2-Asymmetric Induction in Radical Reactions : Radical Addition to γ-Hydroxy α, β-Unsaturated Carboxylic Esters and Sulfones

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High 1,2-asymmetric induction was realized by the addition of a 1-hydroxy-1-methylethyl radical to conformationally flexible (<i>E</i>)-<i>γ</i>-hydroxy <i>α</i>,<i>β</i>-unsaturated carboxylic esters and sulfones (<b>1</b> and <b>2</b>, respectively). Upon the irradiation (> 290 nm) of (<i>E</i>)-<b>1</b> and benzophenone in 2-propanol, the 1-hydroxy-1-methylethyl radical was generated in situ and added to (<i>E</i>)-<b>1</b> with high <i>anti</i>-stereoselectivity. The bulkier is the <i>γ</i>-alkyl group of (<i>E</i>)-<b>1</b>, the higher does the selectivity become. Similarly, a radical addition to the acetates of (<i>E</i>)-<b>1</b> and (<i>E</i>)-<b>2</b> proceeded stereoselectively in an <i>anti</i> fashion, whereas (<i>Z</i>)-<b>2</b> exhibited <i>syn</i>-stereoselectivity. The mechanism for these stereoselective radical additions is discussed.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 70(12), 3091-3101, 1997-12-15

    The Chemical Society of Japan

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  • NII論文ID(NAID)
    10008926763
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • NDL 記事登録ID
    4371019
  • NDL 雑誌分類
    ZP1(科学技術--化学・化学工業)
  • NDL 請求記号
    Z53-B35
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    CJP書誌  NDL  J-STAGE 
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