Catalytic enantioselective synthesis of chiral tetraphenylenes

Consecutive inter- and intramolecular cycloadditions of two triynes

Takanori Shibata, Tatsuya Chiba, Hiroyuki Hirashima, Yasunori Ueno, Kohei Endo

    Research output: Contribution to journalArticle

    44 Citations (Scopus)

    Abstract

    Triynes having a phenylene-bridged 1,5-diyne moiety were transformed into substituted tetraphenylenes by the title sequence. A cationic Rh-ligand species catalyzed this highly enantioselective reaction. This protocol is a new and easy approach to the construction of the tetraphenylene skeleton and enables an efficient asymmetric synthesis (see scheme; R=H; Z=NTs, C(CO2Me) 2, O).

    Original languageEnglish
    Pages (from-to)8066-8069
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume48
    Issue number43
    DOIs
    Publication statusPublished - 2009 Oct 12

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    Cycloaddition
    Ligands

    Keywords

    • Alkynes
    • Asymmetric synthesis
    • Chirality
    • Cycloaddition
    • Rhodium

    ASJC Scopus subject areas

    • Chemistry(all)
    • Catalysis

    Cite this

    Catalytic enantioselective synthesis of chiral tetraphenylenes : Consecutive inter- and intramolecular cycloadditions of two triynes. / Shibata, Takanori; Chiba, Tatsuya; Hirashima, Hiroyuki; Ueno, Yasunori; Endo, Kohei.

    In: Angewandte Chemie - International Edition, Vol. 48, No. 43, 12.10.2009, p. 8066-8069.

    Research output: Contribution to journalArticle

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