Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

Emi Saito, Yuri Matsumoto, Akihiko Nakamura, Yuki Namera, Masahisa Nakada

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    The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.

    元の言語English
    ページ(範囲)692-695
    ページ数4
    ジャーナルOrganic Letters
    20
    発行部数3
    DOI
    出版物ステータスPublished - 2018 2 2

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    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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