Rhodium-complex-catalyzed [2+2+2] cycloaddition of diynes and carbonyl compounds

Kyoji Tsuchikama, Yusuke Yoshinami, Takanori Shibata

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    Abstract

    A Rh-BINAP complex was used to catalyze the hetero-[2+2+2] cycloaddition of symmetrical 1,6-diynes and carbonyl moiety of ketoesters, a diketone, and an aldehyde to give bicyclic α-pyrans, which were readily transformed into monocyclic compounds via the following electrocyclic ring opening. In the reaction of an unsymmetrical 1,6-diyne and a 1,7-diyne, α-pyrans with a quaternary carbon stereocenter were obtained in moderate to excellent ee using a chiral rhodium catalyst.

    Original languageEnglish
    Pages (from-to)1395-1398
    Number of pages4
    JournalSynlett
    Issue number9
    DOIs
    Publication statusPublished - 2007 Jun 1

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    Keywords

    • Carbonyl
    • Catalysis
    • Cycloadditions
    • Diynes
    • Rhodium

    ASJC Scopus subject areas

    • Organic Chemistry

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