{"id":72290,"date":"2018-03-09T23:17:02","date_gmt":"2018-03-09T23:17:02","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/aplicacion-de-sulfoxidos-alfa-beta-insaturados-en-reacciones-de-claisen-diels-alder-y-adicion-nucleofila\/"},"modified":"2018-03-09T23:17:02","modified_gmt":"2018-03-09T23:17:02","slug":"aplicacion-de-sulfoxidos-alfa-beta-insaturados-en-reacciones-de-claisen-diels-alder-y-adicion-nucleofila","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/aplicacion-de-sulfoxidos-alfa-beta-insaturados-en-reacciones-de-claisen-diels-alder-y-adicion-nucleofila\/","title":{"rendered":"Aplicaci\u00f3n de sulf\u00f3xidos alfa-beta insaturados en reacciones de claisen, diels-alder y adici\u00f3n nucle\u00f3fila."},"content":{"rendered":"<h2>Tesis doctoral de <strong> Mariola Tortosa Manzanares <\/strong><\/h2>\n<p>A lo largo de las dos \u00faltimas d\u00e9cadas la utilizaci\u00f3n de sulf\u00f3xidos enantiom\u00e9ricamente puros en s\u00edntesis asim\u00e9trica ha experimentado un crecimiento exponencial, convirtiendo al grupo sulfinilo en uno de los auxiliares quirales m\u00e1s eficaces y vers\u00e1tiles para la formaci\u00f3n  stereocontrolada de enlaces c-c y c-x. dentro de los distintos tipos de compuestossulfin\u00edlicos, los sulf\u00f3xidos ,alfa-beta insaturados constituyen uno de los grupos m\u00e1s utilizados en s\u00edntesis asim\u00e9trica. En esta tesis doctoral se han utilizado sulf\u00f3xidos como auxiliares quirales en distintos procesos siguiendo siempre un objetivo com\u00fan: e[ desarrollo de nuevos m\u00e9todos de s\u00edntesis asim\u00e9trica que permitan la participaci\u00f3n del grupo sulfinilo en posteriores transformaciones diastereoselectivas.  en el cap\u00edtulo 2 de la tesis se describen con detalle las transposiciones de claisen de sulfinil acrilatos y otros alil-sulfinil vinil \u00e9teres. En el proceso se obtienen aldeh\u00eddos y cetonas ,con uno o dos nuevos centros quirales y adem\u00e1s se regenera la unidad de vinil sulf\u00f3xido. En muchos casos el sulf\u00f3xido permite llevar a cabo la reacci\u00f3n a temperaturas no muy elevadas y en tiempos relativamente cortos sin utilizar ning\u00fan tipo de catalizador.  se ha demostrado que en los z-sulfinil acr\u00edlatos el sustituyente en c-5 es capaz de invertir el curso estereoqu\u00edmico, forzando al sustituyente alilico a ocupar una disposici\u00f3n pseudoaxial en un estado de transici\u00f3n tipo silla. Cabe destacar que esta inversi\u00f3n es muy poco frecuente y s\u00f3lo existen dos precedentes en la bibliograf\u00eda.  en el cap\u00edtulo 3 se ha desarrollado un m\u00e9todo de s\u00edntesis enantioselectiva de hidroxi 2-sulfinil dienos a partir de sulfinil c[orhidrinas. La combinaci\u00f3n de una metalaci\u00f3n estereoselectiva dirigida por el grupo sulfinilo seguida de la eliminaci\u00f3n sin del oxirano permite controlar la geometr\u00eda del nuevo doble enlace trisustituido en e[ dieno generado. A continuaci\u00f3n se ha e<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Aplicaci\u00f3n de sulf\u00f3xidos alfa-beta insaturados en reacciones de claisen, diels-alder y adici\u00f3n nucle\u00f3fila.<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Aplicaci\u00f3n de sulf\u00f3xidos alfa-beta insaturados en reacciones de claisen, diels-alder y adici\u00f3n nucle\u00f3fila. <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Mariola Tortosa Manzanares <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Aut\u00f3noma de Madrid<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 14\/01\/2005<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<h3>Direcci\u00f3n y tribunal<\/h3>\n<ul>\n<li><strong>Director de la tesis<\/strong>\n<ul>\n<li> Fern\u00e1ndez De La Pradilla S\u00e1inz De Aja Roberto<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: gregorio Asensio aguilar <\/li>\n<li>victor Mat\u00edn Garc\u00eda (vocal)<\/li>\n<li>Miguel \u00e1ngel Yus astiz (vocal)<\/li>\n<li>Antonio Urbano pujol (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Mariola Tortosa Manzanares A lo largo de las dos \u00faltimas d\u00e9cadas la utilizaci\u00f3n de sulf\u00f3xidos enantiom\u00e9ricamente puros [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"site-sidebar-layout":"default","site-content-layout":"","ast-site-content-layout":"","site-content-style":"default","site-sidebar-style":"default","ast-global-header-display":"","ast-banner-title-visibility":"","ast-main-header-display":"","ast-hfb-above-header-display":"","ast-hfb-below-header-display":"","ast-hfb-mobile-header-display":"","site-post-title":"","ast-breadcrumbs-content":"","ast-featured-img":"","footer-sml-layout":"","theme-transparent-header-meta":"","adv-header-id-meta":"","stick-header-meta":"","header-above-stick-meta":"","header-main-stick-meta":"","header-below-stick-meta":"","astra-migrate-meta-layouts":"default","ast-page-background-enabled":"default","ast-page-background-meta":{"desktop":{"background-color":"var(--ast-global-color-4)","background-image":"","background-repeat":"repeat","background-position":"center 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