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

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


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Publikationens författare: Yury Brusentsev, Thomas Sandberg, Matti Hotokka, Rainer Sjöholm, Patrik Eklund
Förläggare: PERGAMON-ELSEVIER SCIENCE LTD
Publiceringsår: 2013
Tidskrift: Tetrahedron Letters
Tidskriftsakronym: TETRAHEDRON LETT
Volym: 54
Nummer: 9
Artikelns första sida, sidnummer: 1112
Artikelns sista sida, sidnummer: 1115
Antal sidor: 4
ISSN: 0040-4039
eISSN: 1873-3581


Abstrakt

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.


Nyckelord

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


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Senast uppdaterad 2020-28-01 vid 06:09