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

A1 Journal article (refereed)

Internal Authors/Editors

Publication Details

List of Authors: Yury Brusentsev, Thomas Sandberg, Matti Hotokka, Rainer Sjöholm, Patrik Eklund
Publication year: 2013
Journal: Tetrahedron Letters
Journal acronym: TETRAHEDRON LETT
Volume number: 54
Issue number: 9
Start page: 1112
End page: 1115
Number of pages: 4
ISSN: 0040-4039
eISSN: 1873-3581


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.


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


Last updated on 2020-08-07 at 07:01