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Rouen, France

INSA de Rouen is a French grande école, that is to say a five-year curriculum which aims to train engineers who possess humane qualities and are well versed in the primary areas of science and engineering. Located in Saint-Étienne-du-Rouvray, on the Madrillet technology center campus, in the suburbs of Rouen, this school accommodates more than 1400 students who specialize in one of the 7 fields which have been available in Rouen for the 3 last years. Wikipedia.


Nie J.,Tianjin University | Guo H.-C.,China Agricultural University | Cahard D.,INSA Rouen | Ma J.-A.,Tianjin University | Ma J.-A.,CAS Shanghai Institute of Organic Chemistry
Chemical Reviews | Year: 2011

Trifluoromethyl aldimines have emerged as powerful building blocks to construct important molecules in many fields of application. The protecting group on the oxygen was installed to prevent the ring closure into the corresponding oxazolidine during preparation of the substrate. This approach toward Cathepsin K inhibitors gives high diastereoselectivity, is suitable for multigram-scale synthesis, is complementary to the in situ generation of imines from oxazolidines. Trifluoroacetaldehyde imines featuring a chiral enantiopure auxiliary present the disadvantage of being self-immolative for the auxiliary because the nitrogen atom is incorporated in the final product and the stereogenic center is lost during the removal step. Trifluoropyruvates are nonenolizable ketones and more electrophilic than ethyl pyruvate due to the electronwithdrawing trifluoromethyl group.


Mongin F.,CNRS Chemistry Institute of Rennes | Harrison-Marchand A.,INSA Rouen
Chemical Reviews | Year: 2013

The article presents generalities concerning the formation and main features of the Mixed AggregAtes (MAA). Alternative ways to metal organo, amido, and/or alkoxo ate compounds, such as magnesates, calciates, manganates, ferrates, nickelates, and zincates, use the corresponding monometallic compounds (cocomplexation approach). The syntheses of mixed-ligand organo, amido, and/or alkoxo heteroMAAs are in general performed by mixing precursors possessing different ligands in appropriate ratios. The structural data of these compounds have been summarized. It is important to note that, in the presence of oxygen during the preparation of metal ate compounds such as magnesates, aluminates, manganates, and zincates, complex structures with oxo or peroxo cores can be formed, and some of them were evidenced by X-ray crystallography.


Harrison-Marchand A.,INSA Rouen | Mongin F.,CNRS Chemistry Institute of Rennes
Chemical Reviews | Year: 2013

Organometallic chemistry is one of the key assets to successfully achieve complex organic transformations. Numerous tools have been conceived and developed to address problems related to the chemo-, regio-, and stereoselectivities of general reactions such as the deprotonation of prochiral species or the creation of C-C bonds. By way of announcement of the concept, it was decided to dedicate this preliminary review (part 1) on the structural knowledge, in the solid state and/or in solution, of oligo-, homo-, and heteroMAAs that are made of lithium, sodium, and potassium species, as well as magnesium, aluminum, and zinc derivatives. With the latter selection covering still a large panel of organo(bi)metallic combinations depicted in the literature, only systems that are the most encountered and discussed by organic chemists and that are either obtained directly by mixing two commercial organometallics routinely used in organic chemistry or very frequently synthesized and easy to access will be depicted.


Martial L.,INSA Rouen
Synlett | Year: 2013

(A) By analogy with already established carbonylation chemistry, 2a Nguyen and co-workers2b have demonstrated that it was possible to develop palladium-catalyzed reactions to combine aryl halides, sulfur dioxide and N-nucleophiles. They have shown for the first time that is possible to prepare C-SO2-N linkages by an aminosulfonylation process using palladium catalysis. With DABSO, the authors achieved aminosulfonylation reactions between a range of aryl iodides and N,N-dialkylhydrazines, providing aryl N-dialkylaminosulfonamides in good to excellent yield (57-93%). (B) Emmet and co-workers3 have shown that DABSO can effectively replace sulfur dioxide gas in a novel palladium-catalyzed aminosulfonylation process. For example, 4-iodotoluene and Naminomorpholine in the presence of DABSO, cesium carbonate, t-Bu3P, Pd(OAc)2 and DABCO in dioxane, yielded the sulfonylhydrazide in 93% yield. Aryl bromides were employed, too, albeit resulting in lower yields. In this report, the authors have extended the scope of the palladium-catalyzed couplings of DABSO with alkenyl and heteroaryl iodides. In addition, other N-nucleophiles could be used. C) Woolen et al. 4 have studied the formation of sulfonamides, sulfamides, and sulfolenes. They have demonstrated that DABSO can effectively replace gaseous sulfur dioxide in a number of established processes. One of them consists of preparing sulfonamides from DABSO with aryl Grignard reagents, followed by treatment with sulfuryl chloride and an amine, to afford sulfonamides in good yield. In another example, when DABSO was combined with various anilines and iodine, the authors successfully synthesized several N,N′- diphenylsulfamides in 63% yield. They finally established that cheletropic addition of DABSO with 2,3-dimethylbutadiene gives access to sulfolene in 80% yield. (D) Ye et al.5 have developed a novel and efficient route to aryl Naminosulfonamides via a palladium-catalyzed three-component coupling of arylboronic acids, sulfur dioxide and hydrazines in presence of dioxygen. Initially, they studied the palladium-catalyzed reaction of 4- methylphenylboronic acid and N-aminomorpholine in the presence of DABSO. Once the ligand, base, solvent and temperature were optimized, they examined a wide range of arylboronic acids and amines under these conditions (E) Waldmann et al.6 have shown that a bromine-lithium exchange with various aryl halides, followed by addition of DABSO, yields an aryl sulfinate. The authors used DABSO as an alternative SO2 source in the reaction mixture. With this methodology, they explored a novel application in the synthesis of aryl sulfonamides toward one-pot sequences. © Georg Thieme Verlag Stuttgart. New York.


Patent
INSA Rouen, French National Center for Scientific Research, University of Rouen and Vfp Therapies | Date: 2014-01-24

A compound of formula (I) in which the dotted lines indicate the presence of at least one double bond; n=0 to 4; R

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