Wermeskerken, J. van (2010) Enantioselective formal. Bachelor's Thesis, Industrial Engineering and Management.
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Abstract
During the 14 weeks of bachelor research a formal aza-Diels-Alder reaction was investigated. The reason for investigating this reaction is that the product, a pyridone, is an important building block in natural product synthesis and pharmaceutical products. This copper(I) catalyzed reaction also requires catalytic amounts of silver(I) and of course a chiral ligand in order to make the reaction enantioselective. Starting with different N-tosylimines using the chiral ligand Josiphos, electronic effects on the reaction were studied, resulting in ee’s up to 78%. The isolated yields were usually around 60-80%. Next to this, four other chiral ligands, 3 phosphoramidites and Taniaphos, were used as well to see their performance in the reaction. In this case only Taniaphos resulted in a moderate ee of 54%.Also the influence of temperature was taken a brief look at, by lowering the temperature from RT to 0°C.
| Item Type: | Thesis (Bachelor's Thesis) |
|---|---|
| Degree programme: | Industrial Engineering and Management |
| Thesis type: | Bachelor's Thesis |
| Language: | English |
| Date Deposited: | 15 Feb 2018 07:44 |
| Last Modified: | 15 Feb 2018 07:44 |
| URI: | https://fse.studenttheses.ub.rug.nl/id/eprint/9438 |
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