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

    8 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

    ASJC Scopus subject areas

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

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