{"id":116836,"date":"2014-12-12T00:00:00","date_gmt":"2014-12-12T00:00:00","guid":{"rendered":"https:\/\/www.deberes.net\/tesis\/sin-categoria\/6-hydroxy-2h-pyran-3-6h-one-derivatives-as-versatile-reagents-in-organocatalytic-and-enantioselective-reactions\/"},"modified":"2014-12-12T00:00:00","modified_gmt":"2014-12-12T00:00:00","slug":"6-hydroxy-2h-pyran-3-6h-one-derivatives-as-versatile-reagents-in-organocatalytic-and-enantioselective-reactions","status":"publish","type":"post","link":"https:\/\/www.deberes.net\/tesis\/quimica-organica\/6-hydroxy-2h-pyran-3-6h-one-derivatives-as-versatile-reagents-in-organocatalytic-and-enantioselective-reactions\/","title":{"rendered":"6-hydroxy-2h-pyran-3 (6h)-one derivatives as versatile reagents in organocatalytic and enantioselective reactions"},"content":{"rendered":"

Tesis doctoral de Ane Orue Da\u00f1obeitia <\/strong><\/h2>\n

The work compiled in this manuscript focuses on the use of versatile 6 hydroxy-2h-pyran-3(6h)-one derivatives as useful polifunctionalized reagents in the development of different organocatalytic enantioselective reactions with \u00c2\u00bf\u00c2\u00bf\u00c2\u00bf-unsaturated aldehydes, in the presence of chiral secondary amine catalysts. In this sense, 5-oxo-5,6-dihydro-2h-pyran-2-yl carboxylates have been employed as suitable substrates to perform a formal [4+2]\/elimination process with a wide range of enals, by exploiting the potential of the dienamine activation manifold, through a dynamic kinetic resolution. Additionally, 6-hydroxy-2h-pyran-3(6h)-one was used as an oxygen-pronucleophile that undergoes an oxa-michael\/michael cascade process with enals, through iminium\/enamine activation, also in a dynamic kinetic resolution. Besides, 1-acetoxyisochroman-4-ones have been employed as oxidopyrylium ylide precursors in order to carry out a [5+2] cycloaddition with enals. The reaction occurred in the presence of a chiral pyrrolidine\/squaramide bifunctional catalyst and under dienamine activation of the enal, affording oxabicyclo[3.2.1]octanes in excellent results. Finally, and as part of a short stay carried out in the laboratories of prof. K. A. Scheidt in northwestern university, i participated in a project directed to the use of a dual activation strategy involving n-heterocyclic carbene catalysis and a second lewis base to perform an enantioselective [4+3] cycloaddition reaction between enals and in situ generated o-quinone methides.<\/p>\n

 <\/p>\n

Datos acad\u00e9micos de la tesis doctoral \u00ab6-hydroxy-2h-pyran-3 (6h)-one derivatives as versatile reagents in organocatalytic and enantioselective reactions<\/strong>\u00ab<\/h3>\n
    \n
  • T\u00edtulo de la tesis:<\/strong>\u00a0 6-hydroxy-2h-pyran-3 (6h)-one derivatives as versatile reagents in organocatalytic and enantioselective reactions <\/li>\n
  • Autor:<\/strong>\u00a0 Ane Orue Da\u00f1obeitia <\/li>\n
  • Universidad:<\/strong>\u00a0 Pa\u00eds vasco\/euskal herriko unibertsitatea<\/li>\n
  • Fecha de lectura de la tesis:<\/strong>\u00a0 12\/12\/2014<\/li>\n<\/ul>\n

     <\/p>\n

    Direcci\u00f3n y tribunal<\/h3>\n
      \n
    • Director de la tesis<\/strong>\n
        \n
      • Efraim Reyes Mart\u00edn<\/li>\n<\/ul>\n<\/li>\n
      • Tribunal<\/strong>\n
          \n
        • Presidente del tribunal: claudio Palomo nicolau <\/li>\n
        • paolo Melchiorre (vocal)<\/li>\n
        • bel\u00e9n Mart\u00edn matute (vocal)<\/li>\n
        • Jos\u00e9 Manuel Gonz\u00e1lez d\u00edaz (vocal)<\/li>\n<\/ul>\n<\/li>\n<\/ul>\n

           <\/p>\n","protected":false},"excerpt":{"rendered":"

          Tesis doctoral de Ane Orue Da\u00f1obeitia The work compiled in this manuscript focuses on the use of versatile 6 hydroxy-2h-pyran-3(6h)-one […]<\/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":[1412,902,12909,416],"tags":[230501,63073,3064,122359,141720,218669],"class_list":["post-116836","post","type-post","status-publish","format-standard","hentry","category-compuestos-heterociclicos","category-estereoquimica-y-analisis-conformacional","category-pais-vasco-euskal-herriko-unibertsitatea","category-quimica-organica","tag-ane-orue-danobeitia","tag-belen-martin-matute","tag-claudio-palomo-nicolau","tag-efraim-reyes-martin","tag-jose-manuel-gonzalez-diaz","tag-paolo-melchiorre"],"_links":{"self":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/116836","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=116836"}],"version-history":[{"count":0,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/posts\/116836\/revisions"}],"wp:attachment":[{"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/media?parent=116836"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/categories?post=116836"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.deberes.net\/tesis\/wp-json\/wp\/v2\/tags?post=116836"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}