Thermal and palladium-catalyzed [3 + 2] synthesis of cyclopentadienone acetals from cyclopropenone acetals and acetylenes

Hiroyuki Isobe, Sota Sato, Takatsugu Tanaka, Hidetoshi Tokuyama, Eiichi Nakamura

    Research output: Contribution to journalArticle

    25 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) Substituted cyclopentadienone acetals (CPDAs) were synthesized by a thermal or palladium-catalyzed [3 + 2] cycloaddition reaction of a substituted cyclopropenone acetal to an electron-deficient acetylene. The synthesis afforded di-, tri-, and tetrasubstituted CPDAs of considerable structural varieties that undergo Diels-Alder reaction to produce bicyclo[2.2.1]heptenes.

    Original languageEnglish
    Pages (from-to)3569-3571
    Number of pages3
    JournalOrganic letters
    Volume6
    Issue number20
    DOIs
    Publication statusPublished - 2004 Sep 30

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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