Study of cis/trans and endo/exo Diastereoselectivity in the [4+3]-Cycloaddition Reaction of 2-Functionalized Furans and Dimethyloxyallyl Cation : Preparation of Versatile Cycloheptane Synthons

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A study on the influence of steric and electronic effects of a function attached at C-2 of furans in the yield and diastereoselectivity of [4+3] cycloaddition reactions with oxyallyl cations is presented. In almost all studied furans a <I>cis</I> diastereospecificity and a high <I>endo</I> diastereoselectivity is observed. Increasing bulkyness of the function attached at C-2 of furans, increases the <I>endo</I> diastereoselectivity, but decreases yield. Increasing the electronic density of the furan system, by an electron donating group attached at C-2, increases yield and diastereoselectivity.

収録刊行物

  • Chemistry letters

    Chemistry letters 1997(9), 847-848, 1997-09

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10002614510
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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