{"id":17855,"date":"2018-03-09T09:06:07","date_gmt":"2018-03-09T09:06:07","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/addicions-conjugades-a-lactames-bicicliques-derivades-del-fenilglicinol-sintesi-en-antioselectiva-de-piperidines-34-i-345-substitua%c2%afdes\/"},"modified":"2018-03-09T09:06:07","modified_gmt":"2018-03-09T09:06:07","slug":"addicions-conjugades-a-lactames-bicicliques-derivades-del-fenilglicinol-sintesi-en-antioselectiva-de-piperidines-34-i-345-substitua%c2%afdes","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/addicions-conjugades-a-lactames-bicicliques-derivades-del-fenilglicinol-sintesi-en-antioselectiva-de-piperidines-34-i-345-substitua%c2%afdes\/","title":{"rendered":"Addicions conjugades a lactames bicicliques derivades del fenilglicinol. sintesi en antioselectiva de piperidines 3,4- i 3,4,5-substitu\u00c1\u00afdes"},"content":{"rendered":"<h2>Tesis doctoral de <strong> Mar\u00eda P\u00e9rez Bosch <\/strong><\/h2>\n<p>La adici\u00f3n conjugada de cianocupratos de orden inferior a las lactamas insaturadas derivadas del fenilglilcinol transcurre con buenos rendimientos y elevada selectividad facial. En aquellas que poseen un sustituyente etilo en posici\u00f3n contigua al carbono electr\u00f3filo del doble enlace proporciona estereoselectivamente productos con una relaci\u00f3n cis entre el sustituyente carbonado introducido y el grupo etilo. Estos resultados pueden justificarse considerando que la conformaci\u00f3n del anillo de piperidina se halla condicionada por la configuraci\u00f3n de un estereocentro, independientemente de la presencia de un sustituyente etilo, y que el ataque del cianocuprato tiene lugar bajo control estereoel\u00e9ctr\u00f3nico proporcionando el producto de control cin\u00e9tico debido a la irreversibilidad de la reacci\u00f3n.  por otro lado, la adici\u00f3n de aniones estabilizados a una lactama insaturada que posee un sustituyente etilo contiguo al carbono electr\u00f3filo del doble proporciona compuestos que guardan una relaci\u00f3n trans entre el sustituyente carbonado introducido en la adici\u00f3n y el grupo etilo. La estereoselectividad observada es atribuible a la reversibilidad de la reacci\u00f3n de adici\u00f3n conjugada de aniones estabilizados, lo que conduce al compuesto termodin\u00e1micamente m\u00e1s estable.  la utilidad sint\u00e9tica de las anteriores reacciones de adici\u00f3n conjugada se ha puesto de manifiesto con la s\u00edntesis enantioselectiva de diversas piperidinas cis- y trans-3,4-disustituidas:  * con la s\u00edntesis del f\u00e1rmaco antidepresivo (-)-paroxetina se demuestra la posibilidad de obtener ambos enanti\u00f3meros de derivados del trans-4-aril-3-piperidinametanol a partir del (r)-fenilglicinol.  * se preparan las 4-arilpiperidinas cis-3,4-disustituidas: (3s, 4s)-3-etil-4-fenilpiperidina, (4s, 5s)-5-etil-4-fenil-2-piperidona, as\u00ed como la piperidina trisustituida (3s, 4r, 5s)-5-etil-4-fenil-3-piperidinametanol.  * se preparan los derivados de la piperidina-4-acetato: cis-(3s,<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Addicions conjugades a lactames bicicliques derivades del fenilglicinol. sintesi en antioselectiva de piperidines 3,4- i 3,4,5-substitu\u00c1\u00afdes<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Addicions conjugades a lactames bicicliques derivades del fenilglicinol. sintesi en antioselectiva de piperidines 3,4- i 3,4,5-substitu\u00c1\u00afdes <\/li>\n<li><strong>Autor:<\/strong>\u00a0 Mar\u00eda P\u00e9rez Bosch <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Barcelona<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 28\/06\/2002<\/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>Mercedes Amat Tus\u00f3n<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: bruno Danieli <\/li>\n<li>josep Bonjoch sese (vocal)<\/li>\n<li>victor sotero Martin garcia (vocal)<\/li>\n<li>enrique D\u00edez barra (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de Mar\u00eda P\u00e9rez Bosch La adici\u00f3n conjugada de cianocupratos de orden inferior a las lactamas insaturadas derivadas del [&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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