Highly stereoselective Michael reduction/intramolecular Michael reaction cascade to synthesize trans-stereodiad comprising an all-carbon quaternary stereogenic center

Tomohiro Fujii, Kohei Orimoto, Masahisa Nakada

    Research output: Contribution to journalArticle

    6 Citations (Scopus)

    Abstract

    A highly stereoselective Michael reduction/intramolecular Michael reaction cascade is described. The cascade is initiated by the regioselective Michael reduction of an α-methylidene ester with L-Selectride. This is followed by the highly stereoselective intramolecular Michael reaction which efficiently constructs a six-membered carbocyclic ring with formation of the trans-stereodiad, composed of an all-carbon quaternary center and a tertiary stereogenic center. The stereoselectivity is perfectly controlled by the choice of alkene geometry in the Michael acceptor.

    Original languageEnglish
    Pages (from-to)1100-1103
    Number of pages4
    JournalTetrahedron Letters
    Volume55
    Issue number5
    DOIs
    Publication statusPublished - 2014 Jan 29

    Fingerprint

    Alkenes
    Esters
    Carbon
    Stereoselectivity
    Geometry
    selectride

    Keywords

    • Cascade
    • Intramolecular
    • Michael
    • Quaternary stereogenic center
    • Stereoselective

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

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    title = "Highly stereoselective Michael reduction/intramolecular Michael reaction cascade to synthesize trans-stereodiad comprising an all-carbon quaternary stereogenic center",
    abstract = "A highly stereoselective Michael reduction/intramolecular Michael reaction cascade is described. The cascade is initiated by the regioselective Michael reduction of an α-methylidene ester with L-Selectride. This is followed by the highly stereoselective intramolecular Michael reaction which efficiently constructs a six-membered carbocyclic ring with formation of the trans-stereodiad, composed of an all-carbon quaternary center and a tertiary stereogenic center. The stereoselectivity is perfectly controlled by the choice of alkene geometry in the Michael acceptor.",
    keywords = "Cascade, Intramolecular, Michael, Quaternary stereogenic center, Stereoselective",
    author = "Tomohiro Fujii and Kohei Orimoto and Masahisa Nakada",
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    T1 - Highly stereoselective Michael reduction/intramolecular Michael reaction cascade to synthesize trans-stereodiad comprising an all-carbon quaternary stereogenic center

    AU - Fujii, Tomohiro

    AU - Orimoto, Kohei

    AU - Nakada, Masahisa

    PY - 2014/1/29

    Y1 - 2014/1/29

    N2 - A highly stereoselective Michael reduction/intramolecular Michael reaction cascade is described. The cascade is initiated by the regioselective Michael reduction of an α-methylidene ester with L-Selectride. This is followed by the highly stereoselective intramolecular Michael reaction which efficiently constructs a six-membered carbocyclic ring with formation of the trans-stereodiad, composed of an all-carbon quaternary center and a tertiary stereogenic center. The stereoselectivity is perfectly controlled by the choice of alkene geometry in the Michael acceptor.

    AB - A highly stereoselective Michael reduction/intramolecular Michael reaction cascade is described. The cascade is initiated by the regioselective Michael reduction of an α-methylidene ester with L-Selectride. This is followed by the highly stereoselective intramolecular Michael reaction which efficiently constructs a six-membered carbocyclic ring with formation of the trans-stereodiad, composed of an all-carbon quaternary center and a tertiary stereogenic center. The stereoselectivity is perfectly controlled by the choice of alkene geometry in the Michael acceptor.

    KW - Cascade

    KW - Intramolecular

    KW - Michael

    KW - Quaternary stereogenic center

    KW - Stereoselective

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