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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Van Meervelt, Luc Bagdziunas, Gintautas Dehaen, Wim Grazulevicius, Juozas Vidas Waghray, Deepali Jacobs, Jeroen |
| Description | Author Affiliation: Waghray D ( Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven (Belgium), Fax: (+32) 16327990.); Bagdziunas G ( Department of Polymer Chemistry and Technology, Kaunas University of Technology, Barsausko 59, LT-51423 Kaunas (Lithuania).); Jacobs J ( Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven (Belgium).); Van Meervelt L ( Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven (Belgium).); Grazulevicius JV ( Department of Polymer Chemistry and Technology, Kaunas University of Technology, Barsausko 59, LT-51423 Kaunas (Lithuania).); Dehaen W ( Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, B-3001 Leuven (Belgium), Fax: (+32) 16327990. wim.dehaen@chem.kuleuven.be.) |
| Abstract | In the present study, we have investigated different strategies for diastereoselective synthesis of thia[n]helicenes. We describe the introduction of different chiral auxiliaries at various positions and investigated their effect in the photocyclization reaction. Different chiral groups were placed at the sterically hindered position of the helical core and their interactions with various solvents and metals like copper were investigated. The use of $Cu^{I}$ salts has led to high diastereoselectivity in the photocyclization process and we were successful in obtaining the thia[5]helicene in enantiomerically pure form in good yield. The single diastereomer obtained was characterized by X-ray crystallography. From the study of the barrier of racemization of these thia[5]helicenes, the stability was found to be comparable to unsubstituted tetrathia[7]helicenes and substituted diazadithia[7]helicenes. This approach provides an easy access to enantiopure helicenes. |
| ISSN | 09476539 |
| e-ISSN | 15213765 |
| Journal | Chemistry - A European Journal |
| Issue Number | 51 |
| Volume Number | 21 |
| Language | English |
| Publisher | Wiley-VCH;ChemPubSoc Europe |
| Publisher Date | 2015-12-14 |
| Publisher Place | Germany |
| Access Restriction | Open |
| Subject Keyword | Chemistry |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry Catalysis |
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