Iridium complex-catalyzed highly enantio- and diastereoselective [2+2+2] cycloaddition for the synthesis of axially chiral teraryl compounds

Takanori Shibata, Takayoshi Fujimoto, Kazuhisa Yokota, Kentaro Takagi

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    158 Citations (Scopus)

    Abstract

    An asymmetric [2+2+2] cycloaddition of an α,ω-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5) when catalyzed by an iridium-chiral phosphine complex. As the products were readily transformed into diol compounds by deprotection without racemization, the present procedure provides access to a new chiral pool of diol compounds with C2 symmetry.

    Original languageEnglish
    Pages (from-to)8382-8383
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume126
    Issue number27
    DOIs
    Publication statusPublished - 2004 Jul 14

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    ASJC Scopus subject areas

    • Chemistry(all)

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