Chelation control through the coordination of an olefinic π-bond to Lewis acid

N. Asao, T. Shimada, Y. Yamamoto

    Research output: Contribution to journalArticlepeer-review

    8 Citations (Scopus)

    Abstract

    The reaction of a 1:1 mixture of ortho-alkenylbenzaldehydes 3 and their para-isomers 4 with Bu3SnH (1 equiv.) in the presence of Me3Al (1 equiv.) resulted in very high (>10:1) to good (3.4:1) chemoselective reduction of 3, giving the ortho-alkenyl benzyl alcohol 5 selectively. Similarly, the highly chemoselective allylation of 3d in the presence of 4d was observed when the mixture was treated with allyltributyltin/Me3Al. The chemoselectivities are most probably due to the bidentate chelation of the Lewis acid to an olefinic π-bond and a lone pair of aldehydes. (C) 2000 Published by Elsevier Science Ltd.

    Original languageEnglish
    Pages (from-to)9533-9536
    Number of pages4
    JournalTetrahedron Letters
    Volume41
    Issue number49
    DOIs
    Publication statusPublished - 2000 Dec 2

    Keywords

    • Alkenes
    • Allylation
    • Carbonyl compounds
    • Chelation
    • Lewis acid
    • Reduction

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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