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Synthesis and structural analysis of sterically hindered chiral 1,4-diol ligands derived from the lignan hydroxymatairesinol
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Feb2013, Vol. 54 Issue 9, p1112-1115. 4p. - Publication Year :
- 2013
-
Abstract
- 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 (−)-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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 54
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 85153125
- Full Text :
- https://doi.org/10.1016/j.tetlet.2012.12.066