Jean-Roger Desmurs

Bismuth(III) Trifluoromethanesulfonate: A Chameleon Catalyst for the Friedel-Crafts Acylation ;

A mechanism for acylations catalyzed by bismuth(III) triflate (1) is proposed in the case of the benzoylation of benzene, toluene, and chlorobenzene. With Bz2O as a reagent, 1 acts as a Lewis acid and allows the benzoylation of toluene. It is almost completely recovered after the reaction. With BzCl, 1 promotes an exchange reaction which generates BzOTf, which is the active species of the benzoylation. In this latter case, the reaction leads to the formation of TfOH which finally reacts with BiCl3 to partially regenerate 1. The power of the Bz2O/1 system is less than that of BzCl/1, which allows not only the benzoylation of toluene but also that of benzene and deactivated chlorobenzene. The activity of 1 is much higher than that of other metallic triflates previously reported, and is comparable with that of TfOH, however it also has the advantage that the triflate moieties are more easily recoverable.

Regioselective ring opening of epoxides by nucleophiles mediated by lithium bistrifluoromethanesulfonimide

Abstract In the presence of LiNTf 2 , epoxides undergo ring opening with high regioselectivity and in good yield when they are treated with nucleophiles such as amines, hydrazines and thiophenol.

Dimeric surfactants: First synthesis of an asymmetrical gemini compound

Abstract The heterodimeric surfactant 1 is synthesized through a 6-step procedure, starting from 1,2-epoxydodecane. The preliminary evaluation of the performances of that asymmetrical gemini representing a new kind of surface-active agents reveals interesting physical properties.

A Formal Synthesis of (−)‐Paroxetine by Enantioselective Ring Enlargement of a Trisubstituted Prolinol

A ring expansion and a radical dehalogenation have been used as the key steps in a formal total synthesis of (−)-paroxetine. The substituted piperidine ring precursor of (−)-paroxetine was generated by means of a stereoselective ring expansion of prolinol. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Ring expansion: formal total synthesis of (−)-paroxetine

Abstract A ring expansion and a radical dehalogenation have been used as the key steps in a formal total synthesis of (−)-paroxetine. A stereoselective ring expansion of prolinol generated the substituted piperidine ring precursor of (−)-paroxetine.

A short formal synthesis of paroxetine. Diastereoselective cuprate addition to a chiral racemic olefinic amido ester

A diastereoselective conjugate addition of an organocopper reagent to a chiral racemic olefinic amido ester has been used as the key step in a formal total synthesis of paroxetine.

Synthesis and surface-active properties of a series of new anionic gemini compounds

Abstract The synthesis of a series of new anionic dimeric amphiphiles 1–5 is described. The CMC and both static and dynamic surface tensions have been measured using the Wilhelmy plate technique and the maximum bubble pressure method. Results are compared to those obtained with the corresponding monomeric surfactants and relevant monomeric or dimeric compounds described in the literature. The relationship between the structural features of the different compounds and their properties is discussed. In particular an increase in the length of the connecting group between the two lipophilic chains lowers the CMC of the compounds which is different from results reported in the literature for other gemini compounds.

ZrCl4-promoted halogen migration during an electrophilic amination of halogenated phenolsElectronic supplementary information (ESI) available: spectroscopic data (1H NMR,13C NMR, IR, MS), mp and elemental analysis (or HRMS) for the products 3 and 4. See http://www.rsc.org/suppdata/cc/b2/b203622c/Dedicated to Professor Waldemar Adam, University of Würzburg, Germany, on the occasion of his 65th birthday.

An electrophilic amination of halogenated phenols with diisopropyl diazenedicarboxylate in the presence of ZrCl4 as a Lewis acid, accompanied by a halogen migration, was demonstrated for the first time; the fluorine, chlorine, bromine, or iodine atom migrated during the amination process under mild reaction conditions.

Highly enantioselective synthesis via dynamic kinetic resolution under transfer hydrogenation using Ru(η6-arene)-N-perfluorosulfonyl-1,2-diamine catalysts: a first insight into the relationship of the ligand’s pKa and the catalyst activity

β-(3,4-Dimethoxyphenyl)serine methyl ester was obtained in high diastereomeric and enantiomeric excesses under transfer hydrogenation using chiral Ru(η6-arene)-N-perfluorosulfonyl-1,2-diamine catalysts.

A short synthesis of cisapride: a gastrointestinal stimulant derived from cis-4-amino-3-methoxypiperidine

Abstract Cisapride was synthesized in seven steps from piperidin-4-one by using a diastereoselective reduction of an α-oximino ether with the complex BH 3 ·THF.