Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis(oxazolinyl)carbazole ligand

Masahiro Inoue, Takahiro Suzuki, Masahisa Nakada

    Research output: Contribution to journalArticle

    154 Citations (Scopus)

    Abstract

    This work describes the development of a new tridentate ligand effective for the asymmetric catalysis of Nozaki-Hiyama allylation and methallylation. Various aldehydes were allylated or methallylated with good enantioselectivity (86-96%), and a key intermediate of calcitriol lactone synthesis was also obtained with excellent diastereoselectivity (97% de, 91%). The enantioselective reaction catalyzed by this Cr-ligand complex is applicable to a broad range of aldehydes and has great potential for natural product synthesis. Another remarkable feature of this ligand is the stability of the Cr-ligand complex which was recovered after the enantioselective reaction and recycled twice without diminishing the enantioselectivity and yield.

    Original languageEnglish
    Pages (from-to)1140-1141
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume125
    Issue number5
    DOIs
    Publication statusPublished - 2003 Feb 5

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    Allylation
    Catalysis
    Ligands
    Enantioselectivity
    Aldehydes
    Calcitriol
    Lactones
    Biological Products
    carbazole

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Asymmetric catalysis of Nozaki-Hiyama allylation and methallylation with a new tridentate bis(oxazolinyl)carbazole ligand. / Inoue, Masahiro; Suzuki, Takahiro; Nakada, Masahisa.

    In: Journal of the American Chemical Society, Vol. 125, No. 5, 05.02.2003, p. 1140-1141.

    Research output: Contribution to journalArticle

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