Lewis acid catalyzed allylstannylation of unactivated alkynes

Yasuhisa Matsukawa, Naoki Asao, Haruo Kitahara, Yoshinori Yamamoto

    Research output: Contribution to journalArticlepeer-review

    55 Citations (Scopus)

    Abstract

    The addition of allyltributylstannane 2 to unactivated aromatic alkynes 1 in the presence of catalytic amounts of ZrCl4 or EtAlCl2 produced the stannylated 1,4-dienes 3 with very high regio- and stereoselectivities in good to high yields. The exclusive trans manner of addition was confirmed by 1H NMR analysis of crude reaction mixtures. On the other hand, the stereochemistries of addition products produced from the reactions using aliphatic acetylenes depended on the reaction conditions and the Lewis acid type. The mechanisms for the ZrCl4 and EtAlCl2 catalyzed allylstannylation of alkynes are proposed.

    Original languageEnglish
    Pages (from-to)3779-3790
    Number of pages12
    JournalTetrahedron
    Volume55
    Issue number12
    DOIs
    Publication statusPublished - 1999 Mar 19

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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