Paul Mosset

Indium-mediated allylation of aldimines

Abstract Aldimines are allylated under simple Barbier type conditions using ally] bromide and indium powder in THF.

Trimethylsulfonium Methylsulfate, A Simple and Efficient Epoxidizing Agent

Abstract Sulfonium salts 1 and 3 are highly reactive epoxidizing agents under phase transfer catalytic conditions.

Sorbic acid iron tricarbonyl complex as resolving agent. Chiralsyntheses of 4-hydroxy nonenal and cariolic acid.

Abstract The chiral iron tricarbonyl complex of sorbic acid 2 is an efficient resolving agent for allylic alcohol 3 , which is a key intermediate in the preparation of most of the lipoxygenation products in n-6 position of polyunsaturated fatty acids. The synthesis of 4-hydroxy nonenal and methyl coriolate, in both enantiomeric forms, illustrates the potential of the method.

Asymmetric cyclopropanation catalyzed by C2-symmetric bi(oxazolines)

Abstract C 2 -symmetric bi(oxazolines) 3a – e were prepared in three steps based on a tartaric-derived vicinal diamine as common precursor. These chiral ligands were studied with respect to their directive influence on the enantioselective copper catalyzed cyclopropanation of 1,1-diphenylethylene and styrene. The highest enantioselectivities (79% ee) were achieved with bi(oxazoline) 3e , bearing bulky adamantyl groups even using commercial CuOTf. The presence of desiccants such as molecular sieves or magnesium sulfate was found to be crucial for high yields and reproducibility.

Multiple beneficial health effects of natural alkylglycerols from shark liver oil.

Alkylglycerols (alkyl-Gro) are ether lipids abundant in the liver of some elasmobranch fish species such as ratfishes and some sharks. Shark liver oil from Centrophorus squamosus (SLO), or alkyl-Gro mix from this source, have several in vivo biological activities including stimulation of hematopoiesis and immunological defences, sperm quality improvement, or anti-tumor and anti-metastasis activities. Several mechanisms are suggested for these multiple activities, resulting from incorporation of alkyl-Gro into membrane phospholipids, and lipid signaling interactions. Natural alkyl-Gro mix from SLO contains several alkyl-Gro, varying by chain length and unsaturation. Six prominent constituents of natural alkyl-Gro mix, namely 12:0, 14:0, 16:0, 18:0, 16:1 n-7, and 18:1 n-9 alkyl-Gro, were synthesized and tested for anti-tumor and anti-metastatic activities on a model of grafted tumor in mice (3LL cells). 16:1 and 18:1 alkyl-Gro showed strong activity in reducing lung metastasis number, while saturated alkyl- Gro had weaker (16:0) or no (12:0, 14:0, 18:0) effect. Multiple compounds and mechanisms are probably involved in the multiple activities of natural alkyl-Gro.

Reverse asymmetric catalytic epoxidation of unfunctionalized alkenes

Abstract New salen Mn(III) complexes (S,S)- 6a-e prepared from tartaric-derived alicyclic C 2 symmetric vicinal diamines were studied in the catalysis of the asymmetric epoxidation of unfunctionalized alkenes. Although the enantioselectivities obtained were not as high as for Jacobsen and Katsuki catalysts, the most striking result was the reversed asymmetric induction.

Synthesis and reactivity of E,Z butadiene-iron tricarbonyl complexes

Abstract The synthesis, structure and thermal stability of the E,Z butadiene-iron tricarbonyl complex 1 is reported. This complex reacts with organometallic nucleophiles in a stereoselective synthesis of functionalized E,Z dienes.

Efficient synthesis of (2R,3R)- and (2S,3S)-2,3-diaminobutane-1,4-diol and their dibenzyl ethers

Abstract (2 R ,3 R )-2,3-Diaminobutane-1,4-diol 6 and its dibenzyl ether 7 were efficiently synthesized starting from L-tartaric acid 1a . The crucial step, debenzylation of intermediate dibenzyloxydiazide 4 , was accomplished in good yield by boron trichloride-dimethyl sulfide complex. The enantiomeric series was similarly obtained starting from D-tartaric acid.

Stereoselective synthesis and Diels-Alder reactions of bis-Ether 1,3 Dienes. A further test for cooperativity during cycloaddition reactions.

A stereoselective synthesis of dienes 1a and 1b, using butadiene-iron tricarbonyl complexes, is described. Higher diastereoselectivity is observed during Diels-Alder reaction of 1a as compared with 1c, affording good evidence for cooperativity in these cycloadditions.

Stereo- and enantioselective synthesis of some e,z dienols and ethers.

Abstract Functionnalized E,Z dienes (−) 2 have been prepared in a highly stereo- and enantioselective manner using chiral pentadienyl iron tricarbonyl complexes 1 .