Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol

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    Abstract

    The readily available natural lignan hydroxymatairesinol was transformed into sterically hindered and optically pure diphenyl, di-2-naphthyl, and tetramethyl 1,4-diol derivatives via mylation/alkylation of the aryltetralinbutyrolactone lignan (-)-conidendrin. In addition, the diastereoselective formation of stable hemiketals from the highly substituted butyrolactone was studied in detail. The conformations of the molecules prepared were studied computationally at molecular mechanics (MM), Hartree-Fock (HF)/6-31G*, and (DFT/B3LYP/TZVP) levels including entropy contributions and by NMR-spectroscopy. The conformations adopted showed that these novel chiral 1,4-diols may be suitable as chiral ligands for the development of new chiral transition metal and organo catalysts.
    Original languageUndefined/Unknown
    Pages (from-to)1112–1115
    Number of pages4
    JournalTetrahedron Letters
    Volume54
    Issue number9
    DOIs
    Publication statusPublished - 2013
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Ab initio calculations
    • Asymmetric catalysis
    • Chiral 1,4-diol
    • Hydroxymatairesinol

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