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

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    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

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    Keywords

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

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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