Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

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

    Research output: Contribution to journalArticle

    9 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)692-695
    Number of pages4
    JournalOrganic Letters
    Volume20
    Issue number3
    DOIs
    Publication statusPublished - 2018 Feb 2

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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