Highly enantioselective catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides

Harufumi Oyama, Kohei Orimoto, Takashi Niwa, Masahisa Nakada

    Research output: Contribution to journalArticle

    7 Citations (Scopus)

    Abstract

    Catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides are described. The rationally designed cyclic α-alkylidene β-oxo imides show high enantioselectivity in the Mukaiyama-Michael reaction using a bisoxazoline/Cu(OTf)2 catalyst. The enantioselectivity can be well explained by the chelate model comprising an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.

    Original languageEnglish
    JournalTetrahedron Asymmetry
    DOIs
    Publication statusAccepted/In press - 2014 Nov 8

    Fingerprint

    Michael reaction
    alkylidene
    Imides
    Enantioselectivity
    imides
    Hydrogen bonds
    Catalysts
    chelates
    hydrogen bonds
    catalysts

    ASJC Scopus subject areas

    • Organic Chemistry
    • Inorganic Chemistry
    • Physical and Theoretical Chemistry
    • Catalysis

    Cite this

    Highly enantioselective catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides. / Oyama, Harufumi; Orimoto, Kohei; Niwa, Takashi; Nakada, Masahisa.

    In: Tetrahedron Asymmetry, 08.11.2014.

    Research output: Contribution to journalArticle

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    AU - Nakada, Masahisa

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    AB - Catalytic asymmetric Mukaiyama-Michael reactions of cyclic α-alkylidene β-oxo imides are described. The rationally designed cyclic α-alkylidene β-oxo imides show high enantioselectivity in the Mukaiyama-Michael reaction using a bisoxazoline/Cu(OTf)2 catalyst. The enantioselectivity can be well explained by the chelate model comprising an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.

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