Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides

Kazuaki Enomoto, Harufumi Oyama, Masahisa Nakada

    研究成果: Article

    22 引用 (Scopus)

    抄録

    Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides are described. The high reactivity of the cyclic α-alkylidene β-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low temperature. The X-ray crystallographic analysis of the product suggests that the enantioselectivity of the [2+2] cycloaddition can be well explained by the chelate model comprising the intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls. The imide group in the product can be transformed to amide, nitrile, and ester groups; moreover, it is removable.

    元の言語English
    ページ(範囲)2798-2802
    ページ数5
    ジャーナルChemistry (Weinheim an der Bergstrasse, Germany)
    21
    発行部数7
    DOI
    出版物ステータスPublished - 2015 2 9

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    Imides
    Cycloaddition
    Cycloaddition Reaction
    Enantioselectivity
    Amides
    Esters
    Hydrogen bonds
    Nitriles
    X rays
    Substrates
    Hydrogen
    X-Rays
    Temperature

    ASJC Scopus subject areas

    • Medicine(all)

    これを引用

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    abstract = "Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides are described. The high reactivity of the cyclic α-alkylidene β-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low temperature. The X-ray crystallographic analysis of the product suggests that the enantioselectivity of the [2+2] cycloaddition can be well explained by the chelate model comprising the intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls. The imide group in the product can be transformed to amide, nitrile, and ester groups; moreover, it is removable.",
    keywords = "asymmetric catalysis, cycloadditions, enantioselectivity, imides, ynamides",
    author = "Kazuaki Enomoto and Harufumi Oyama and Masahisa Nakada",
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    AU - Enomoto, Kazuaki

    AU - Oyama, Harufumi

    AU - Nakada, Masahisa

    PY - 2015/2/9

    Y1 - 2015/2/9

    N2 - Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides are described. The high reactivity of the cyclic α-alkylidene β-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low temperature. The X-ray crystallographic analysis of the product suggests that the enantioselectivity of the [2+2] cycloaddition can be well explained by the chelate model comprising the intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls. The imide group in the product can be transformed to amide, nitrile, and ester groups; moreover, it is removable.

    AB - Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides are described. The high reactivity of the cyclic α-alkylidene β-oxo imide allows the [2+2] cycloadditions of a hindered substrate with unreactive ynamides at low temperature. The X-ray crystallographic analysis of the product suggests that the enantioselectivity of the [2+2] cycloaddition can be well explained by the chelate model comprising the intramolecular hydrogen bond, wherein the cyclic α-alkylidene β-oxo imide coordinates with Cu(II) through the two imide carbonyls. The imide group in the product can be transformed to amide, nitrile, and ester groups; moreover, it is removable.

    KW - asymmetric catalysis

    KW - cycloadditions

    KW - enantioselectivity

    KW - imides

    KW - ynamides

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