Catalytic Asymmetric Additions of Carbon-Centered Nucleophiles to Nitrogen-Containing Aromatic Heterocycles

Muneer Ahamed, Matthew Todd

    Research output: Contribution to journalReview articlepeer-review

    66 Citations (Scopus)

    Abstract

    Nearly a century after the first report of the Reissert reaction the first catalytic, asymmetric example was published. Since then there have been a small number of reports of similar reaction types: activation of nitrogen-containing aromatic rings through alkylation or acylation, followed by the addition of a carbon-centered nucleophile to the ring. These reactions place great demands on catalyst design; many of the catalysts are bifunctional, simultaneously activating both nucleophiles and electrophiles. The structures obtained from such reactions may easily be derivatized into natural products or drug-like structures. Despite the elegance of the known examples, there are still many reaction types that have not been reported. In the last decade a small number of highly effective methods have been developed for the catalytic asymmetric addition ofcarbon-based nucleophiles to aromatic nitrogen heterocycles. The resulting structures are of wide potential utility in synthetic and medicinal chemistry. There is a great deal of room for discovery of new reactions in this class.

    Original languageEnglish
    Pages (from-to)5935-5942
    Number of pages8
    JournalEuropean Journal of Organic Chemistry
    Volume2010
    Issue number31
    DOIs
    Publication statusPublished - Nov 2010

    Keywords

    • Asymmetric catalysis
    • Bifunctional catalysis
    • Nitrogen heterocycles
    • Nucleophilic addition

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