{"id":61672,"date":"2018-03-09T22:49:33","date_gmt":"2018-03-09T22:49:33","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/synthetic-applications-of-enantipure-expoxides-preparation-of-new-ligands-for-asymmetric-catalysis-and-a-chiral-resolution-agent\/"},"modified":"2018-03-09T22:49:33","modified_gmt":"2018-03-09T22:49:33","slug":"synthetic-applications-of-enantipure-expoxides-preparation-of-new-ligands-for-asymmetric-catalysis-and-a-chiral-resolution-agent","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica-organica\/synthetic-applications-of-enantipure-expoxides-preparation-of-new-ligands-for-asymmetric-catalysis-and-a-chiral-resolution-agent\/","title":{"rendered":"Synthetic applications of enantipure expoxides: preparation of new ligands for asymmetric catalysis and a chiral resolution agent"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Sergi Rodriguez Escrich <\/strong><\/h2>\n<p>A partir de la publicaci\u00f3n por parte de oguni y omi, que explicaba la primera adici\u00f3n de dietilzinc a benzaldehido catalizada por (s)- leucinol con un 49% de exceso enantiom\u00e9trico (ee), la investigaci\u00f3n en la adici\u00f3n enantioselectiva de organoz\u00edncicos a cabonilo ha demostrado un enorme desarrollo. Nuestro grupo de investigaci\u00f3n ha trabajado intensamente en este campo durante los \u00faltimos a\u00f1os, originando diversas familias de ligandos con un esqueleto de ?-Amino alcohol, desarrolladas con \u00e9xito partiendo de ep\u00f3xidos enantiom\u00e9ricamente puros. Concretamente el ligando 2-piperidino-1,1,2-trifeniletanol demostr\u00f3 ser altamente activo en las adiciones de organoz\u00edncicos a carbonilo. Por ello en este trabajo se ha llevado a cabo un estudio de optimizaci\u00f3n de su estructura hall\u00e1ndose otras dos ligados an\u00e1logos. Una de ellos con un grupo amino c\u00edclico de siete eslabones, y el de otra adem\u00e1s con un cloro en posici\u00f3n meta en el anilo arom\u00e1tico contiguo. Se ha llevado a cabo un estudio comparativo de los tres ligandos en las adiciones de etilo, metilo y fenilo sobre diversos aldeh\u00eddos, siendo el ligando de referencia el que dio lugar a resultados m\u00e1s consistentes. nuestro grupo de investigaci\u00f3n tambi\u00e9n ha mostrado gran inter\u00e9s en ligandos con estructura aminoindanol para inducir quiralidad en la adici\u00f3n de dietilzinc a benzaldehido. En este trabajo se han preparado derivados de los 4 is\u00f3meros posibles con esqueleto de aminoindanol, resultando los derivados del cis-2-amino-1-indanol los que han dado lugar a mayores enantioselectividades. En cambio, en la alquilaci\u00f3n ar\u00edlica (como derivado de bisoxazolina), en la reducci\u00f3n asim\u00e9trica de cetonas( como oxazaborolidina), en la adici\u00f3n de cianuro de trimetilsililo(como derivado de inmina) y en la hidrogenaci\u00f3n por transferencia de cetonas, han sido los derivados del cis-1amino-2-indanol con los que se han obtenido mejores resultados. Paralelamente, se ha sintetizado un fluoroep\u00f3xido como agente quiral de derivatizaci\u00f3n para la determinaci\u00f3n del ee de aminas escal\u00e9micas, como elevada fiabilidad tanto por resonancia de fluor como por hplc, sacando partido de la presencia de un grupo crom\u00f3foro en su estructura. De este modo se han derivatizado con \u00e9xito aminas benc\u00edlicas, una mina alif\u00e1tica, amino alcoholes y amino esteres, sin observarse en ning\u00fan caso resoluci\u00f3n cin\u00e9tica. A partir del mismo fluoroep\u00f3xido se sintetiz\u00f3 un derivado de glucosalina con una cadena fluorada, el cual ha dado resultados positivos como sonda molecular por su interacci\u00f3n con glicosidasas.<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Synthetic applications of enantipure expoxides: preparation of new ligands for asymmetric catalysis and a chiral resolution agent<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Synthetic applications of enantipure expoxides: preparation of new ligands for asymmetric catalysis and a chiral resolution agent <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Sergi Rodriguez Escrich <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 30\/11\/2007<\/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>Miguel \u00e1ngel Peric\u00c1\u00a0s Brondo<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: albert Moyano baldoire <\/li>\n<li>ant\u00f3n Vidal i ferran (vocal)<\/li>\n<li>miriam Royo exp\u00f3sito (vocal)<\/li>\n<li>Jes\u00fas Jim\u00e9nez-barbero (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Sergi Rodriguez Escrich A partir de la publicaci\u00f3n por parte de oguni y omi, que explicaba la [&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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