Gold-catalyzed carbon-carbon, carbon-oxygen and carbon-nitrogen bond formations : efficient synthesis of isoflavanones, aza-isoflavanones, [plus or minus symbol]-pterocarpans and isoflavones

Note: === Recent years have witnessed a tremendous growth in the number of goldcatalyzeddevelop new gold catalytic methods to mediate carbon-carbon, carbon-oxygenand carbon-nitrogen bond forming reactions. Chapter 2 describes new annulations catalyzed by gold(I) of simple 0-hydroxyaldehydes with al...

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Bibliographic Details
Main Author: Skouta, Rachid
Other Authors: Li, Chao-Jun (Supervisor)
Format: Others
Language:en
Published: McGill University 2008
Subjects:
Online Access:http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=109697
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Summary:Note: === Recent years have witnessed a tremendous growth in the number of goldcatalyzeddevelop new gold catalytic methods to mediate carbon-carbon, carbon-oxygenand carbon-nitrogen bond forming reactions. Chapter 2 describes new annulations catalyzed by gold(I) of simple 0-hydroxyaldehydes with alkynes. This annulation efficiently generates isoflavanone-type structures, which have many possible applications in the synthesis of isoflavanone natural products. This chapter details the development and the optimization of the reaction conditions. The annulation was applied to various aldehydes and arylalkynes with good efficiency. Furthermore, it incorporated all atoms of both starting materials into the product and thus has a theoretical atom economy of 100%. Chapter 3 extends the scope of the annulations developed in Chapter 2. Indeed, 2,3-dihydro-l-tosylquinolin-3(1H)-one derivatives, aza-isoflavanones, have been efficiently synthesized via a gold-catalyzed annulation of 2-tosylaminobenzaldehyde and alkynes. The annulation was applied to various arylalkynes with good efficiency. This annulation can be used for the synthesis of a range of potentially bioactive molecules. [...] === Récemment nous avons constate une énorme croissance de l'utilisation de l'or comme nouveau catalyseur dans de nombreuses transformations chimiques sélectives. Le but de cette étude était de développer de nouvelles méthodes catalytiques en utilisant I' or pour former de nouveaux liens carbone-carbone, carbone-oxygène et carbone-azote. Dans le chapitre 2, nous décrirons la nouvelle addition catalysée par Por(I) entre des 2-hydroxyaldehydes et des alcynes. Cette addition produit des structures de type isoflavanones efficacement. Ces derniers sont impliques dans la synthèse de nombreux produits nature Is. L' addition a été appliquée efficacement diversaldéhydes et alcynes. En outre, l'addition a incorpore tous les atomes des produits de départ au produit final et a ainsi une économie d'atome théorique de 100%. Le développement et l'optimisation des conditions de réaction seront détailles dans ce chapitre.[...]