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

Tsuyoshi Ueda, Nobuhiro Kanomata, Hajime Machida

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    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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    ASJC Scopus subject areas

    • Molecular Medicine

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