Organic Syntheses

Organic Syntheses is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and experiments reported in an article must be successfully repeated in the laboratory of a member of the editorial board as a check for reproducibility prior to publication. The journal is published by Organic Syntheses, Inc., a non-profit corporation. An annual print version is published by John Wiley & Sons on behalf of Organic Syntheses, Inc. History Prior to World War I, work on synthetic organic chemistry in the United States had been quite limited, and most of the reagents used in laboratories had to be imported from Europe. When export stoppages and trade embargoes cut off this source, Clarence Derick, a professor of chemistry at University of Illinois at Urbana-Champaign, began an effort to synthesize these needed chemicals in industri

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Exploitation of Unconventional Electrophiles in Enantioselective Pd(0)-Catalyzed C-H Functionalizations

Daria Grosheva

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

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

Total Synthesis of Aspidosperma Family Indole Alkaloids through the iORC Domino Process

Olivier Wagnières

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

Organic chemistry

Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various

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