Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5266240 | Tetrahedron Letters | 2013 | 4 Pages |
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 arylation/alkylation of the aryltetralinbutyrolactone lignan (â)-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)/6-31Gâ, 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.
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Authors
Yury Brusentsev, Thomas Sandberg, Matti Hotokka, Rainer Sjöholm, Patrik Eklund,