Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines

Ichiro Minami, Yukihiro Ohashi, Isao Shimizu, Jiro Tsuji

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    Abstract

    Allylation of carbonucleophiles with allylic carbamates under neutral conditions has been studied. The C-allylation of carbonucleophile is competitive with the N-allylation of amines, and the structure of amines is crucial for the selectivity. Bulky secondary amines gave the best results. Also a new method of protection-deprotection of amines as carbamates has been developed. Smooth deprotection is possible by the palladium-catalyzed reaction of allyl carbamates with formic acid. This method is particulary useful for primary amines, including optically active amino acids.

    Original languageEnglish
    Pages (from-to)2449-2452
    Number of pages4
    JournalTetrahedron Letters
    Volume26
    Issue number20
    DOIs
    Publication statusPublished - 1985

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    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

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