Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides

Harufumi Oyama, Masahisa Nakada

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides with indole, pyrrole, and furan derivatives at relatively low temperatures are described. The X-ray crystallographic analysis of the product revealed that the sense of enantioselectivity of the Friedel-Crafts reactions could be well explained by the proposed chelate model. The model was stabilized by an intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls.

    Original languageEnglish
    Pages (from-to)195-202
    Number of pages8
    JournalTetrahedron Asymmetry
    Volume26
    Issue number4
    DOIs
    Publication statusPublished - 2015 Feb 28

    Fingerprint

    Friedel-Craft reaction
    Friedel-Crafts reaction
    alkylidene
    Imides
    imides
    Enantioselectivity
    Hydrogen bonds
    Pyrroles
    furans
    indoles
    pyrroles
    Derivatives
    chelates
    X rays
    hydrogen bonds
    products
    Temperature
    x rays

    ASJC Scopus subject areas

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

    Cite this

    Highly enantioselective catalytic Friedel-Crafts reactions of cyclic α-alkylidene β-oxo imides. / Oyama, Harufumi; Nakada, Masahisa.

    In: Tetrahedron Asymmetry, Vol. 26, No. 4, 28.02.2015, p. 195-202.

    Research output: Contribution to journalArticle

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