Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction

Hiroko Sekita, Kyohei Adachi, Ippei Kobayashi, Yusuke Sato, Masahisa Nakada

    Research output: Contribution to journalArticle

    2 Citations (Scopus)

    Abstract

    An enantio- and stereoselective construction of the atisane scaffold via organocatalytic intramolecular Michael reaction and Diels-Alder reaction is described. The organocatalytic intramolecular Michael reaction has been found to stereoselectively generate a trans-stereodiad comprising an all-carbon quaternary and a tertiary stereogenic centers. Use of the chiral secondary amine bearing thiourea with benzoic acid as additive is the key to obtaining the desired product with excellent ee in synthetically acceptable yield. The prepared chiral building block has been successfully converted to the compound including the atisane scaffold via the highly stereoselective intramolecular Diels-Alder reaction.

    Original languageEnglish
    Pages (from-to)2390-2393
    Number of pages4
    JournalOrganic Letters
    Volume19
    Issue number9
    DOIs
    Publication statusPublished - 2017 May 5

    Fingerprint

    Michael reaction
    Diels-Alder reactions
    Cycloaddition Reaction
    Scaffolds
    Bearings (structural)
    Thiourea
    Benzoic Acid
    thioureas
    benzoic acid
    Amines
    amines
    Carbon
    carbon
    products

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

    Cite this

    Enantio- and Stereoselective Construction of Atisane Scaffold via Organocatalytic Intramolecular Michael Reaction and Diels-Alder Reaction. / Sekita, Hiroko; Adachi, Kyohei; Kobayashi, Ippei; Sato, Yusuke; Nakada, Masahisa.

    In: Organic Letters, Vol. 19, No. 9, 05.05.2017, p. 2390-2393.

    Research output: Contribution to journalArticle

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    AU - Sato, Yusuke

    AU - Nakada, Masahisa

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