Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals

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

    Research output: Contribution to journalArticle

    6 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

    Fingerprint

    quinones
    Amino Alcohols
    Cyclization
    synthesis
    alcohols
    Bearings (structural)
    Diels-Alder reactions
    Phenols
    Cycloaddition Reaction
    Alkenes
    phenols
    alkenes
    Electrons
    preparation
    benzoquinone
    products
    electrons

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals. / Saito, Emi; Matsumoto, Yuri; Nakamura, Akihiko; Namera, Yuki; Nakada, Masahisa.

    In: Organic Letters, Vol. 20, No. 3, 02.02.2018, p. 692-695.

    Research output: Contribution to journalArticle

    Saito, E, Matsumoto, Y, Nakamura, A, Namera, Y & Nakada, M 2018, 'Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals', Organic Letters, vol. 20, no. 3, pp. 692-695. https://doi.org/10.1021/acs.orglett.7b03824
    Saito, Emi ; Matsumoto, Yuri ; Nakamura, Akihiko ; Namera, Yuki ; Nakada, Masahisa. / Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals. In: Organic Letters. 2018 ; Vol. 20, No. 3. pp. 692-695.
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