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dc.contributor.advisorCarrillo Fernández, María Luisa ORCID
dc.contributor.advisorVicario Hernando, José Luis ORCID
dc.contributor.authorFernández Hernández, Naiara
dc.contributor.otherQuímica Orgánica II/Kimika Organikoa IIes
dc.date.accessioned2014-01-21T15:28:37Z
dc.date.available2014-01-21T15:28:37Z
dc.date.issued2014-01-21T15:28:37Z
dc.date.submitted2012-10-26
dc.identifier.urihttp://hdl.handle.net/10810/11231
dc.description.abstractDuring the research that it is summarized in the present memory, the activation of enals via iminium ion catalysis in different transformations has been studied. Firstly, a 1,3-dipolar cycloaddition between stable azomethine ylides and a,b-unsaturated aldehydes catalyzed by a chiral imidazolidinone derivative has been optimized. Employing this methodology we have synthesized a large range of densely substituted pyrroloisoquinolines and pyrrolophthalazines with good yields and high values of diastereo- and enantioselectivity. Moreover, a mechanistic study has been carried out based on DFT calculations and experimental data which have allowed us to propose that the (3+2) cycloaddition reaction follows a sequential Michael addition/Mannich cyclization pathway. The formation of the iminium ion as a result of the condensation between the a,b-unsaturated aldehyde and the catalyst plays an essential role, regarding both reactivity and stereoselectivity. On the other hand we have developed a methodology to carry out a cascade Michael/Henry reaction followed by a sequential dehydration. Starting from simple substrates (2-nitromethylacrilates and a,b-unsaturated aldehydes) and employing a prolinol-derivative catalyst a series of quiral nitrocyclohexadienes have been synthesized.es
dc.language.isospaes
dc.language.isoenges
dc.rightsinfo:eu-repo/semantics/openAccesses
dc.subjectsíntesis estereocontroladaes
dc.subjectcicloadición (3+2)es
dc.subjectreacción Michael/Henry en cascada.es
dc.titleActivación de aldehídos a,b-insaturados mediante aminocatálisis en procesos enantioselectivos. Cicloadiciones (3+2) y reacciones en cascada Michael/Henryes
dc.typeinfo:eu-repo/semantics/doctoralThesises
dc.identifier.studentID286502es
dc.identifier.projectID485es
dc.departamentoesQuímica orgánica IIes_ES
dc.departamentoeuKimika organikoa IIes_ES


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