{"id":76129,"date":"2005-09-09T00:00:00","date_gmt":"2005-09-09T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/estudio-de-la-reactividad-de-alil-o-litioaril-eteres-sa%c2%adntesis-diastereo-y-enantioselectiva-de-derivados-de-ciclopropano-y-23-dihidrobenzofurano\/"},"modified":"2005-09-09T00:00:00","modified_gmt":"2005-09-09T00:00:00","slug":"estudio-de-la-reactividad-de-alil-o-litioaril-eteres-sa%c2%adntesis-diastereo-y-enantioselectiva-de-derivados-de-ciclopropano-y-23-dihidrobenzofurano","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica\/estudio-de-la-reactividad-de-alil-o-litioaril-eteres-sa%c2%adntesis-diastereo-y-enantioselectiva-de-derivados-de-ciclopropano-y-23-dihidrobenzofurano\/","title":{"rendered":"Estudio de la reactividad de alil o-litioaril \u00e9teres. s\u00edntesis diastereo- y enantioselectiva de derivados de ciclopropano y 2,3-dihidrobenzofurano"},"content":{"rendered":"<h2>Tesis doctoral de <strong> C\u00e9sar Marcos Moneo <\/strong><\/h2>\n<p>Las reacciones de carbolitiaci\u00f3n intramolecular proporcionan una ruta regioespec\u00edfica y altamente estereoselectiva para la preparaci\u00f3n de sistemas carboc\u00edclicos y heteroc\u00edclicos funcionalizados selectivamente. Adem\u00e1s, el reciente desarrollo de su versi\u00f3n enantioselectiva ha aumentado de manera significativa su potencial sint\u00e9tico.  en este contexto, y dado el inter\u00e9s de nuestro grupo de investigaci\u00f3n por la preparaci\u00f3n y aplicaciones sint\u00e9ticas de derivados organol\u00edticos funcionalizados, se ha estudiado la reactividad de alil y bencil o-litioaril \u00e9teres, lo que ha permitido, variando \u00fanicamente el disolvente empleado o el patr\u00f3n de sustituci\u00f3n en el ani\u00f3n de partida, el desarrollo de nuevas estrategias sint\u00e9ticas para la preparaci\u00f3n de diferentes tipos de compuestos org\u00e1nicos.  as\u00ed, la evoluci\u00f3n en et2o, hexano o tolueno en presencia de tmeda de los organol\u00edticos derivados de alil o-bromoaril \u00e9teres sin sustituyentes carbonados en la posici\u00f3n   respecto al \u00e1tomo de ox\u00edgeno o en la posici\u00f3n 6 del anillo arom\u00e1tico da lugar, de forma diastereoselectiva, a derivados de ciclopropano mediante una ciclaci\u00f3n regioselectiva 5-exo-trig seguida de un proceso de  -eliminaci\u00f3n en los 3-litiometil-2,3-dihidrobenzofuranos intermedios. adem\u00e1s, esta reacci\u00f3n puede llevarse a cabo de forma enantioselectiva mediante la adici\u00f3n de un ligando externo enantiom\u00e9ricamente puro, tal como la (-)-esparte\u00edna.  sin embargo, la presencia de un sustituyente en la posici\u00f3n   respecto al \u00e1tomo de ox\u00edgeno en el organol\u00edtico de partida permite detener el proceso tras la carbolitiaci\u00f3n intramolecular, lo que ha conducido a una metodolog\u00eda sencilla, eficaz y totalmente diastereoselectiva para la s\u00edntesis de trans-2, 3-dihidrobenzofuranos 2,3-disustituidos. Cabe destacar que, cuando en la reacci\u00f3n intervienen alil 2-litiofenil \u00e9teres enriquecidos enantiom\u00e9ricamente, los heterociclos finales presentan el mismo exceso enantiom<\/p>\n<p>&nbsp;<\/p>\n<h3>Datos acad\u00e9micos de la tesis doctoral \u00ab<strong>Estudio de la reactividad de alil o-litioaril \u00e9teres. s\u00edntesis diastereo- y enantioselectiva de derivados de ciclopropano y 2,3-dihidrobenzofurano<\/strong>\u00ab<\/h3>\n<ul>\n<li><strong>T\u00edtulo de la tesis:<\/strong>\u00a0 Estudio de la reactividad de alil o-litioaril \u00e9teres. s\u00edntesis diastereo- y enantioselectiva de derivados de ciclopropano y 2,3-dihidrobenzofurano <\/li>\n<li><strong>Autor:<\/strong>\u00a0 C\u00e9sar Marcos Moneo <\/li>\n<li><strong>Universidad:<\/strong>\u00a0 Burgos<\/li>\n<li><strong>Fecha de lectura de la tesis:<\/strong>\u00a0 09\/09\/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> Sanz D\u00edez Roberto Jos\u00e9<\/li>\n<\/ul>\n<\/li>\n<li><strong>Tribunal<\/strong>\n<ul>\n<li>Presidente del tribunal: josep Font cierco <\/li>\n<li>Jos\u00e9 Luis Mascare\u00f1as cid (vocal)<\/li>\n<li>Rafael Pedrosa saez (vocal)<\/li>\n<li>felix Rodr\u00edguez iglesias (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Tesis doctoral de C\u00e9sar Marcos Moneo Las reacciones de carbolitiaci\u00f3n intramolecular proporcionan una ruta regioespec\u00edfica y altamente estereoselectiva para la 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