Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling

Tsuyoshi Ueda, Nobuhiro Kanomata, Hajime Machida

    Research output: Contribution to journal › Article

    56 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) A series of [n]jparacyclophanediols (n = 8-12) was synthesized by samarium-catalyzed pinacol coupling for their ansa-bridge formation. Enantiomerically pure [n]jparacyclophane esters were derived from the diols in a several steps via chiral resolution (for n = 10) or via crystallization-induced asymmetric transformation (for n = 11) by using amino alcohol auxiliaries and their selective cleavages.

    Original languageEnglish
    Pages (from-to)2365-2368
    Number of pages4
    JournalOrganic Letters
    Volume7
    Issue number12
    DOIs
    Publication statusPublished - 2005 Jun 9

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    Samarium
    Amino Alcohols
    samarium
    Crystallization
    esters
    cleavage
    Esters
    alcohols
    crystallization
    synthesis

    ASJC Scopus subject areas

    • Molecular Medicine

    Cite this

    Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling. / Ueda, Tsuyoshi; Kanomata, Nobuhiro; Machida, Hajime.

    In: Organic Letters, Vol. 7, No. 12, 09.06.2005, p. 2365-2368.

    Research output: Contribution to journal › Article

    Ueda, T, Kanomata, N & Machida, H 2005, 'Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling', Organic Letters, vol. 7, no. 12, pp. 2365-2368. https://doi.org/10.1021/ol0506258
    Ueda T, Kanomata N, Machida H. Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling. Organic Letters. 2005 Jun 9;7(12):2365-2368. https://doi.org/10.1021/ol0506258
    Ueda, Tsuyoshi ; Kanomata, Nobuhiro ; Machida, Hajime. / Synthesis of planar-chiral paracyclophanes via samarium(II)-catalyzed intramolecular pinacol coupling. In: Organic Letters. 2005 ; Vol. 7, No. 12. pp. 2365-2368.
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