{"id":89810,"date":"2018-03-10T00:15:04","date_gmt":"2018-03-10T00:15:04","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/sa%c2%adntesis-enantioselectiva-de-alfa-aminoacidos-por-expoxidacion-o-aminohidroxilacion-asimetrica-de-harpless\/"},"modified":"2018-03-10T00:15:04","modified_gmt":"2018-03-10T00:15:04","slug":"sa%c2%adntesis-enantioselectiva-de-alfa-aminoacidos-por-expoxidacion-o-aminohidroxilacion-asimetrica-de-harpless","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/sa%c2%adntesis-enantioselectiva-de-alfa-aminoacidos-por-expoxidacion-o-aminohidroxilacion-asimetrica-de-harpless\/","title":{"rendered":"S\u00edntesis enantioselectiva de alfa-amino\u00e1cidos por expoxidaci\u00f3n o aminohidroxilaci\u00f3n asim\u00e9trica de harpless"},"content":{"rendered":"<h2>Tesis doctoral de <strong>  Medina Fuentes Eva M <\/strong><\/h2>\n<p>La presente tesis doctoral consta de tres cap\u00edtulos. En el primero de ellos se han preparado dos n-boc-alfa-arilglicinas con excelentes enantiom\u00e9ricos (la d-n-boc-1-naftilglicina y la n-boc-mesitilglicina, amino\u00e1cidos de gran importancia biol\u00f3gica ya que han constituido antibi\u00f3ticos como las cefalosporinas y las nocardicinas), utilizando y optimizando la metodolog\u00eda ya desarrollada en nuestro grupo de investigaci\u00f3n para este tipo de compuestos.  esta se basa en la expoxidaci\u00f3n catal\u00edtica de sharpless sobre alcoholes al\u00edlicos, en la apertura totalmente regio y estereoselectiva de los epoxialcoholes formados con equivalentes sint\u00e9ticos del amon\u00edaco (concretamente con azida s\u00f3dica y bajo las condiciones de crotti y con benzhidrilamina en presencia de tetraisoprop\u00f3xido de titanio) y en la rotura oxidativa del grupo diol de n-boc-aminodiol obtenido en el paso anterior. As\u00ed mismo, se ha comprobado que esta metodolog\u00eda es perfectamente aplicable a la preparaci\u00f3n de n-fmoc-alfa-arilglicinas enantiom\u00e9ricamente puras aunque adaptando alguna de las etapas de la secuencia sint\u00e9tica.  finalmente se ha preparado dos ariloxazolidinonas a partir de las dos n-boc-alfa-arilglicinas preparadas mediante la secuencia de esterificaci\u00f3n y reducci\u00f3n del grupo \u00e1cido carbox\u00edlico y ciclaci\u00f3n del aminoalcohol resultante utilizando el grupo protector amino como puente en el cierre del ciclo.  en el segundo cap\u00edtulo se ha realizado un exhaustivo estudio de la reacci\u00f3n de aminohidroxilaci\u00f3n catal\u00edtica asim\u00e9trica de sharpless, la cual consiste en la oxidaci\u00f3n enantioselectiva de uan olefina a un beta-aminoalcohol o beta-amino-alfa-hidroxiester.  una vez concretadas sus ventajas e inconvenientes se ha utilizado dicha reacci\u00f3n para la preparaci\u00f3n de sustancias de inter\u00e9s farmacol\u00f3gico como los alfa-amino\u00e1cidos, un precursor de is\u00f3steres de dip\u00e9ptido y l-treo-esfingosinas. en la s\u00edntesis de estos compuestos se ha utilizado la reacci<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>S\u00edntesis enantioselectiva de alfa-amino\u00e1cidos por expoxidaci\u00f3n o aminohidroxilaci\u00f3n asim\u00e9trica de harpless<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 S\u00edntesis enantioselectiva de alfa-amino\u00e1cidos por expoxidaci\u00f3n o aminohidroxilaci\u00f3n asim\u00e9trica de harpless <\/li>\n<li><strong>Autor:<\/strong>\u00a0  Medina Fuentes Eva M <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 20\/04\/2001<\/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>Antoni Riera Escale<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: Miguel \u00e1ngel Peric\u00ed\u00a0s brondo <\/li>\n<li>s. Mart\u00edn v\u00edctor (vocal)<\/li>\n<li>Fernando Albericio palomera (vocal)<\/li>\n<li>albert Virgili (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Medina Fuentes Eva M La presente tesis doctoral consta de tres cap\u00edtulos. En el primero de ellos [&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 center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"ast-content-background-meta":{"desktop":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"tablet":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""},"mobile":{"background-color":"var(--ast-global-color-5)","background-image":"","background-repeat":"repeat","background-position":"center center","background-size":"auto","background-attachment":"scroll","background-type":"","background-media":"","overlay-type":"","overlay-color":"","overlay-gradient":""}},"footnotes":""},"categories":[1104,951,160,17],"tags":[186693,1382,1099,186691,19695,186692],"class_list":["post-89810","post","type-post","status-publish","format-standard","hentry","category-aminoacidos","category-barcelona","category-bioquimica","category-quimica","tag-albert-virgili","tag-antoni-riera-escale","tag-fernando-albericio-palomera","tag-medina-fuentes-eva-m","tag-miguel-angel-perici-s-brondo","tag-s-martin-victor"],"_links":{"self":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/89810","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/comments?post=89810"}],"version-history":[{"count":0,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/89810\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/media?parent=89810"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/categories?post=89810"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/tags?post=89810"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}