Asymmetric epoxidation of unfunctionalised alkenes catalysed by d-fructose derivatives
In this thesis we focus on the synthesis of enantiopure epoxides using D-fructose derivatives as catalysts. A practical synthesis of the previously reported Shi’s diester catalyst (4,5-Di-O-acetyl-1,2-O-isopropylidene-D-erythro--2,3-hexadiulo-2,6-pyrano-se) was developed. Synthetic aspects such as...
| Autor: | |
|---|---|
| Tipo de recurso: | tesis doctoral |
| Estado: | Versión publicada |
| Fecha de publicación: | 2013 |
| País: | España |
| Institución: | Universitat Rovira i virgili (URV) |
| Repositorio: | Repositori Institucional de la Universitat Rovira i Virgili |
| OAI Identifier: | oai:urv.cat:TDX:1291 |
| Acceso en línea: | https://hdl.handle.net/20.500.11797/TDX1291 http://hdl.handle.net/10803/128208 |
| Access Level: | acceso abierto |
| Palabra clave: | 547 - Química orgànica 54 - Química |
| Sumario: | In this thesis we focus on the synthesis of enantiopure epoxides using D-fructose derivatives as catalysts. A practical synthesis of the previously reported Shi’s diester catalyst (4,5-Di-O-acetyl-1,2-O-isopropylidene-D-erythro--2,3-hexadiulo-2,6-pyrano-se) was developed. Synthetic aspects such as selectivity, efficiency, cost and environmental issues of the reagents were taken into account. Optimisation of the work-up allowed for the isolation of its dihydrate derivative (no described previously). The epoxidation conditions using both D-fructose derivatives (diester and its hydrate) were optimised. Both catalysts were subsequently assayed in the asymmetric epoxidation of an array of unfunctionalised alkenes obtaining high activities and enantioselectivities. Finally, labelling experiments provided a sound understanding of the stereoinduction processes. |
|---|