Enantioselective synthesis of planar-chiral phosphines with 1,n-dioxa[n]paracyclophane scaffold and their application as chiral ligands

Kazumasa Kanda, Shoya Oshima, Tsubasa Shizuno, Risa Hamanaka, Miku Fukai, Takanori Shibata

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    A new family of chiral phosphines based on planar-chiral 1,n-dioxa[n]paracyclophane scaffold was created. They were synthesized with excellent enantioselectivity via asymmetric ortho-lithiation using sec-butyllithium and (-)-sparteine. These phosphines were used as chiral ligands in three reactions: Ag-catalyzed allylation of imines, Pd-catalyzed asymmetric Sonogashira coupling of diiodoparacyclophanes, and Pd-catalyzed asymmetric Suzuki-Miyaura coupling of tricarbonyl(η6-ortho-dichlorobenzene)chromium.

    Original languageEnglish
    Pages (from-to)1355-1370
    Number of pages16
    JournalHeterocycles
    Volume8
    Issue number2
    DOIs
    Publication statusPublished - 2014

    Fingerprint

    Phosphines
    Scaffolds
    Sparteine
    Allylation
    Ligands
    Imines
    Enantioselectivity
    Chromium
    butyllithium

    ASJC Scopus subject areas

    • Analytical Chemistry
    • Pharmacology
    • Organic Chemistry

    Cite this

    Enantioselective synthesis of planar-chiral phosphines with 1,n-dioxa[n]paracyclophane scaffold and their application as chiral ligands. / Kanda, Kazumasa; Oshima, Shoya; Shizuno, Tsubasa; Hamanaka, Risa; Fukai, Miku; Shibata, Takanori.

    In: Heterocycles, Vol. 8, No. 2, 2014, p. 1355-1370.

    Research output: Contribution to journalArticle

    Kanda, Kazumasa ; Oshima, Shoya ; Shizuno, Tsubasa ; Hamanaka, Risa ; Fukai, Miku ; Shibata, Takanori. / Enantioselective synthesis of planar-chiral phosphines with 1,n-dioxa[n]paracyclophane scaffold and their application as chiral ligands. In: Heterocycles. 2014 ; Vol. 8, No. 2. pp. 1355-1370.
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    AU - Fukai, Miku

    AU - Shibata, Takanori

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