[2+2+2] cycloaddition reactions involving allenes catalysed by rhodium
The development of new chemical processes for the formation of carbon-carbon bonds is an important topic in organic chemistry. In particular, the transition metal catalysed [2+2+2] cycloaddition reaction is a highly efficient synthetic tool that allows six-membered polysubstituted carbo- and heteroc...
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| Tipo de recurso: | tesis doctoral |
| Estado: | Versión publicada |
| Fecha de publicación: | 2015 |
| País: | España |
| Institución: | CBUC, CESCA |
| Repositorio: | TDR. Tesis Doctorales en Red |
| OAI Identifier: | oai:www.tdx.cat:10803/328439 |
| Acceso en línea: | http://hdl.handle.net/10803/328439 |
| Access Level: | acceso abierto |
| Palabra clave: | Catàlisi de metalls de transició Transition metal catalysis Catalizadores metálicos de transición Cycloaddition Cicloaddició Cicloaddición Allenes Al·lens Alenos Rhodium Rodio Rodi 547 |
| Sumario: | The development of new chemical processes for the formation of carbon-carbon bonds is an important topic in organic chemistry. In particular, the transition metal catalysed [2+2+2] cycloaddition reaction is a highly efficient synthetic tool that allows six-membered polysubstituted carbo- and heterocyclic derivatives to be obtained in an atom economy process. Allenes are versatile substrates for cycloaddition reactions that provide a good reactivity profile together with the ability to increase the stereochemical complexity of the cycloadducts obtained. This doctoral thesis, divided into seven different chapters, is based on the methodological study of the rhodium(I)-catalysed [2+2+2] cycloaddition reaction involving allenes. Chapter 1 contains a general introduction to the structural and reactivity particularities of allenes and to the [2+2+2] cycloaddition reactions, making reference to the main examples found in the literature. Chapter 2 sets out the general objectives of the thesis. In Chapters 3 and 4 the reactivity of linear chiral and non-chiral allene-ene/yne-allene substrates in totally intramolecular rhodium-catalysed [2+2+2] cycloaddition is evaluated. In Chapter 5, a dehydrogenative [2+2+2] cycloaddition of cyano-yne-allene substrates is developed which allows for the synthesis of the 2,6-naphthyridines core found in biologically relevant products. Chapter 6 draws general conclusions from the results of these studies. Finally, Chapter 7 contains the experimental procedure and the characterization data for the compounds synthesised in this thesis. |
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