Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 10, Pages 1985-1992Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001699
Keywords
Oxidation; Stereoselectivity; Triphenylene ketals
Categories
Funding
- Deutsche Forschungsgemeinschaft (DFG) [SFB 624]
- CHANNEL program
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The stereoselective synthesis of triphenylene ketals offers access to unique scaffolds. For a good performance in supramolecular applications an all-syn orientation of the functional groups is essential. The oxidative trimerization of catechol ketals by molybdenum pentachloride or mixtures with titanium tetrachloride leads to a template-directed formation. Several heterocyclic moieties are suitable for this transformation. A template-directed isomerization of anti,anti,syn isomers to the desired C-3-symmetric derivative was demonstrated in two cases.
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