Highly diastereoselective desymmetrizing intramolecular cyclization of allylstannane with a diketone promoted by Lewis acid or transition metal complex

Takashi Shimada, Naoki Asao, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    4 Citations (Scopus)

    Abstract

    The Lewis acid mediated de symmetrizing intramolecular cyclization of prochiral allylstannyl diketone (1) gave a mixture of two diastereomers (2 and 3). Highly diastereoselective synthesis of each of the diastereomers was accomplished by appropriate choice of the Lewis acid. Compound 3 was also produced stereoselectively by using a palladium catalyst instead of Lewis acid.

    Original languageEnglish
    Pages (from-to)136-142
    Number of pages7
    JournalJournal of Organometallic Chemistry
    Volume624
    Issue number1-2
    DOIs
    Publication statusPublished - 2001 Apr 1

    Keywords

    • Allylstannane
    • Desymmetrizing cyclization
    • Diketone
    • Lewis acid
    • Transition metal catalyst

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry
    • Materials Chemistry

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