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

Ichiro Minami, Yukihiro Ohashi, Isao Shimizu, Jiro Tsuji

    Research output: Contribution to journalArticle

    84 Citations (Scopus)

    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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    Allylation
    Palladium
    Amines
    formic acid
    Carbamates
    allyl carbamate
    Amino Acids

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines. / Minami, Ichiro; Ohashi, Yukihiro; Shimizu, Isao; Tsuji, Jiro.

    In: Tetrahedron Letters, Vol. 26, No. 20, 1985, p. 2449-2452.

    Research output: Contribution to journalArticle

    Minami, Ichiro ; Ohashi, Yukihiro ; Shimizu, Isao ; Tsuji, Jiro. / Palladium-catalyzed reaction of allyl carbamates; allylation of carbonucleophiles, and protection-deprotection of amines. In: Tetrahedron Letters. 1985 ; Vol. 26, No. 20. pp. 2449-2452.
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    AU - Tsuji, Jiro

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