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

Kazuaki Enomoto, Harufumi Oyama, Masahisa Nakada

    Research output: Contribution to journalArticle

    22 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)2798-2802
    Number of pages5
    JournalChemistry (Weinheim an der Bergstrasse, Germany)
    Volume21
    Issue number7
    DOIs
    Publication statusPublished - 2015 Feb 9

    Fingerprint

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

    Keywords

    • asymmetric catalysis
    • cycloadditions
    • enantioselectivity
    • imides
    • ynamides

    ASJC Scopus subject areas

    • Medicine(all)

    Cite this

    Highly enantioselective catalytic asymmetric [2+2] cycloadditions of cyclic α-alkylidene β-oxo imides with ynamides. / Enomoto, Kazuaki; Oyama, Harufumi; Nakada, Masahisa.

    In: Chemistry (Weinheim an der Bergstrasse, Germany), Vol. 21, No. 7, 09.02.2015, p. 2798-2802.

    Research output: Contribution to journalArticle

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