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 language | Undefined/Unknown |
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Pages (from-to) | 1112–1115 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 54 |
Issue number | 9 |
DOIs | |
Publication status | Published - 2013 |
MoE publication type | A1 Journal article-refereed |
Keywords
- Ab initio calculations
- Asymmetric catalysis
- Chiral 1,4-diol
- Hydroxymatairesinol