Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides

Kohei Orimoto, Harufumi Oyama, Yuki Namera, Takashi Niwa, Masahisa Nakada

    Research output: Contribution to journal › Article

    28 Citations (Scopus)

    Abstract

    Highly enantioselective catalytic asymmetric reactions of rationally designed α-alkylidene β-keto imides are described. The [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides proceed with high enantioselectivity and yield. The [4 + 2] cycloadditions of the imides with various dienes afford products bearing an all-carbon quaternary stereogenic center at the ring junction. α-Alkylidene β-keto imides should be useful for the enantioselective total synthesis of natural products and other catalytic asymmetric applications.

    Original languageEnglish
    Pages (from-to)768-771
    Number of pages4
    JournalOrganic Letters
    Volume15
    Issue number4
    DOIs
    Publication statusPublished - 2013 Feb 15

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    alkylidene
    Imides
    Cycloaddition
    imides
    Cycloaddition Reaction
    cycloaddition
    Bearings (structural)
    Enantioselectivity
    dienes
    products
    Biological Products
    Carbon
    carbon
    rings
    synthesis

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry
    • Biochemistry

    Cite this

    Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides. / Orimoto, Kohei; Oyama, Harufumi; Namera, Yuki; Niwa, Takashi; Nakada, Masahisa.

    In: Organic Letters, Vol. 15, No. 4, 15.02.2013, p. 768-771.

    Research output: Contribution to journal › Article

    Orimoto, K, Oyama, H, Namera, Y, Niwa, T & Nakada, M 2013, 'Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides', Organic Letters, vol. 15, no. 4, pp. 768-771. https://doi.org/10.1021/ol303381c
    Orimoto K, Oyama H, Namera Y, Niwa T, Nakada M. Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides. Organic Letters. 2013 Feb 15;15(4):768-771. https://doi.org/10.1021/ol303381c
    Orimoto, Kohei ; Oyama, Harufumi ; Namera, Yuki ; Niwa, Takashi ; Nakada, Masahisa. / Catalytic asymmetric [4 + 2] cycloadditions and Hosomi-Sakurai reactions of α-alkylidene β-keto imides. In: Organic Letters. 2013 ; Vol. 15, No. 4. pp. 768-771.
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    AU - Nakada, Masahisa

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