A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters

Jiro Tsuji, Kiyomi Sakai, Hideo Nagashima, Isao Shimizu

    Research output: Contribution to journalArticle

    34 Citations (Scopus)

    Abstract

    A new synthetic method for γ-acetoxy-α,β-unsaturated esters by the acetoxylation of β,γ-unsaturated esters catalyzed by PdCl2 in the presence of KOAc and pentyl nitrite in acetic acid is presented. The reaction takes place at γ-position of the esters regioselectively with double bond migration to α,β-position. The E configuration of the double bond was confirmed by NMR analysis. Preliminary investigation to synthesize pyrenophorin and pyrenophorol using this reaction is described.

    Original languageEnglish
    Pages (from-to)131-134
    Number of pages4
    JournalTetrahedron Letters
    Volume22
    Issue number2
    DOIs
    Publication statusPublished - 1981

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    Palladium
    Esters
    Nitrites
    Acetic Acid
    Nuclear magnetic resonance

    ASJC Scopus subject areas

    • Biochemistry
    • Organic Chemistry
    • Drug Discovery

    Cite this

    A novel synthetic method for γ-acetoxy-(E)-α,β-unsaturated esters by the palladium catalyzed regio- and stereoselective acetoxylation of β,γ-unsaturated esters. / Tsuji, Jiro; Sakai, Kiyomi; Nagashima, Hideo; Shimizu, Isao.

    In: Tetrahedron Letters, Vol. 22, No. 2, 1981, p. 131-134.

    Research output: Contribution to journalArticle

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