Kluifhooft, Robert (2022) Towards Photoswitchable Asymmetric Phase-Transfer Fluorination using Urea Functionalized First-Generation Molecular Motors. Master's Thesis / Essay, Chemistry.
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Abstract
Fluorine has become a widely investigated atom in drug design, medicinal and agro chemistry. This, because incorporation of the atom accompanies some favorable properties such as enhanced binding interactions, metabolic stability and altered physicochemical properties. Over the past few decades, advances have been made in the use of molecular motors for (switchable) catalysis. However, a molecular motor has never been used for the synthesis of C-F stereogenic centers. In this work, a newly optimized route towards the synthesis of enantiomerically pure urea-type molecular motors has been developed. The synthesis involves the use of an efficient optical resolution process of a hydroxyl-motor intermediate. Subsequent transformations resulted in optically pure motor catalysts. The bisurea-motors were used in the asymmetric fluorination of an episulfonium substrate with cesium fluoride as a cheap and abundant fluoride source. Conversion of up to 99% was achieved to the desired fluoride compound. Enantioselectivity was obtained by adding small amounts of BINAP to the reaction, which resulted in selectivities of up to 50% ee.
| Item Type: | Thesis (Master's Thesis / Essay) |
|---|---|
| Supervisor name: | Stindt, C.N. |
| Degree programme: | Chemistry |
| Thesis type: | Master's Thesis / Essay |
| Language: | English |
| Date Deposited: | 27 Jun 2022 12:45 |
| Last Modified: | 27 Jun 2022 12:45 |
| URI: | https://fse.studenttheses.ub.rug.nl/id/eprint/27375 |
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