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Synthesis of all ‐ syn Functionalized Triphenylene Ketals
Author(s) -
Boshta Nader M.,
Bomkamp Martin,
Schnakenburg Gregor,
Waldvogel Siegfried R.
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001699
Subject(s) - triphenylene , chemistry , catechol , derivative (finance) , stereoselectivity , isomerization , supramolecular chemistry , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , molecule , financial economics , economics
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.