Organic Syntheses

Résumé

Organic Syntheses (abrégé en Org. Synth.) est une revue scientifique à comité de lecture en libre accès fondée en 1921 et qui publie annuellement des procédures détaillées et vérifiées de synthèses de composés organiques à destination de la communauté des chimistes. Historique L'histoire d'Organic Syntheses débute en 1914 avec la Première Guerre mondiale. Du fait du conflit, les États-Unis sont coupés des fournisseurs européens qui fournissent la plupart des produits chimiques nécessaires à la recherche américaine. En réponse à cet état de fait, l'Université de l'Illinois à Urbana-Champaign met en place des summer preps au cours desquels des étudiants travaillent à l'amélioration des méthodes de synthèse pour la recherche en chimie. Parmi les composés chimiques dont le besoin se fait le plus sentir figurent par exemple les colorants pour films photographiques. L'effort de recherche dans ce domaine pousse à la création de la division Chimie organique de Kodak. Les summer p

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https://fr.wikipedia.org/wiki/Organic_Syntheses

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Asymmetric metal-catalyzed C-H functionalization has enjoyed great success as a powerful strategy for the rapid construction of elaborate structures from simple precursors. For example, aryl (pseudo)halides have been extensively employed as electrophilic substrates in enantioselective Pd(0)-catalyzed syntheses of heterocycles. However, alternative substrates for C-H functionalizations are far less developed. This thesis focuses on the exploration of unconventional electrophilic partners for asymmetric Pd(0)-catalyzed C-H functionalizations, allowing access to relevant N-heterocyclic scaffolds. An enantioselective functionalization of readily accessible ketene aminal phosphates resulted in the formation of versatile isoindolines. A new class of bulky electron-rich phosphine ligands, designed explicitly for this transformation, enabled efficient functionalization at ambient temperature, resulting in high enantioselectivities of the desired products. Employing perfluoroalkyl imidoyl chlorides as electrophilic partners gave rise to previously inaccessible chiral 1H-isoindoles. The C-H functionalization strategy not only enabled efficient asymmetric construction of three-dimensional structures with functional exit vectors but also allowed the products to be additionally decorated with a perfluoroalkyl group and a quaternary stereogenic center.

EPFL2019

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Syntheses, structures and properties of cobalt and manganese complexes based on pyridine-2,3,5,6-tetracarboxylic acid

Chi Wai Cheung, Hong-Ling Gao, Weijin Wang

Two new complexes based on pyridine-2,3,5,6-tetracarboxylic acid(H(4)pdtc) as ligand, {[Co-2(pdtc)(H2O)(4)]center dot H2O}(n) (1) and {Mn-2(pdtc)(H2O)(4)}(n) (2), have been obtained by hydrothermal syntheses and characterized by IR, elemental analysis, X-ray diffraction single crystal structure analysis, PXRD, thermal gravimetric analysis, and magnetic measurements. Complex 1 is 3D coordination polymer and complex 2 belongs to 2D grid structure by covalent bonds. In 1 and 2, the metal ions show antiferromagnetic interactions. (C) 2015 Elsevier B.V. All rights reserved.

Elsevier Science Bv2015

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This thesis describes a unified strategy for the synthesis of monoterpene indole alkaloids of the Aspidosperma family. These syntheses feature two key steps: (1) a palladiumcatalyzed decarboxylative vinylation that provides quick access to cyclopentene intermediates containing all of the carbons present in the natural products and (2) an integrated oxidation/reduction/cyclization (iORC) sequence for skeletal reorganisation that converts the cyclopentenes to the corresponding pentacyclic structures of the natural products. By incorporation of a geometric constraint to the iORC substrates, both the chemoselectivity (C7 versus N1 cyclization) and the stereoselectivity (trans- versus cis-fused ring system) of the cyclization process can be controlled. Using this method, we achieved the racemic total synthesis of aspidospermidine and dehydroaspidospermidine in seven steps; both of which feature a cis-fused ring system. We then accomplished a ten-steps synthesis of kopsihainanine A featuring a trans-fused ring system. The work towards the total synthesis of aspidoalbidine and kopsinitarine E using the same two key steps was attempted, but was not completed in the time provided. This PhD will also cover our synthetic efforts towards the alkaloidminfiensine, featuring a domino reduction/cyclization sequence performed prior to the development of the iORC process.

EPFL2015

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