Dokument: Frustrated Lewis Pair-Catalysed Functionalisation of Alkenes with Iodoperfluoroalkanes and Gold-Catalysed Desymmetrisation of 1,4-Diynes
| Titel: | Frustrated Lewis Pair-Catalysed Functionalisation of Alkenes with Iodoperfluoroalkanes and Gold-Catalysed Desymmetrisation of 1,4-Diynes | |||||||
| URL für Lesezeichen: | https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=50212 | |||||||
| URN (NBN): | urn:nbn:de:hbz:061-20190718-095905-1 | |||||||
| Kollektion: | Dissertationen | |||||||
| Sprache: | Englisch | |||||||
| Dokumententyp: | Wissenschaftliche Abschlussarbeiten » Dissertation | |||||||
| Medientyp: | Text | |||||||
| Autor: | Spittler, Michael [Autor] | |||||||
| Dateien: |
| |||||||
| Beitragende: | Prof. Dr. Czekelius, Constantin [Gutachter] PD Dr. Schaper, Klaus [Gutachter] | |||||||
| Dewey Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik » 540 Chemie | |||||||
| Beschreibung: | This doctoral dissertation describes work in the field of Frustrated Lewis Pair (FLP) chemistry and a total synthesis of Mesembrine.
Firstly, FLP-systems were investigated which are capable to iodoperfluoralkylate molecules bearing functional groups like amides, esters and ethers. For this purpose electronically tuned phosphanes as well as boranes were synthesised. Next, various phosphanes and solvents were screened. For an elucidation of the mechanism, kinetic studies including a treatment of catalyst degradation pathways were performed. By several test reactions radical intermediates were proven. Terminal alkynes as well as electron-poor alkenes were subjected to iodoperfluoroalkylations. Besides these FLP-catalysed reactions, an iodoperfluoroalkylation utilising solely tri-tert-butylphosphane under the influence of sunlight was established for 9-decen-ol, 1-octyne and phenylacetlyene. Secondly, a total synthesis of (+)-mesembrine was condcuted starting from 4-bromoveratrole with a surprisingly challenging synthesis of a 1,4-diynamide as the key intermediate. This diynamide was successfully subjected to a gold-catalysed enantioselective desymmetrisation to build up a methylene pyrrolidine comprising a quaternary stereocentre. | |||||||
| Lizenz: |  Urheberrechtsschutz | |||||||
| Fachbereich / Einrichtung: | Mathematisch- Naturwissenschaftliche Fakultät » WE Chemie » Organische Chemie und Makromolekulare Chemie | |||||||
| Dokument erstellt am: | 18.07.2019 | |||||||
| Dateien geändert am: | 18.07.2019 | |||||||
| Promotionsantrag am: | 12.12.2018 | |||||||
| Datum der Promotion: | 28.01.2019 |
