Pascal Gosselin
Centre national de la recherche scientifique
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Featured researches published by Pascal Gosselin.
Tetrahedron Letters | 1980
Pascal Gosselin; Serge Masson; A. Thuillier
Abstract Methyl propenedithioate and three methyl 2-butenedithioates were prepared and all but one of these hetero-dienes gave dimers resulting from a [4 + 2] cycloaddition. Formation of a 1,5-dithiocin ring was also observed from the propenedithioate.
International Journal of Environmental Analytical Chemistry | 2000
Cecile Baudin; Christophe Péan; Bruno Perly; Pascal Gosselin
Abstract Both (−)-geosmin and (+)-2-methyl-isoborneol are the main compounds responsible for the unpleas-and smells found in the vicinity of water-processing plant. Attempts to eliminate them using oxidation, filtration and/or biologic degradation processes are only partly efficient. The use of cage molecules could provide an alternative solution. In this respect, cyclodextrins and derivatives have demonstrated their role as candidates as hosts for these highly hydrophobic compounds. In this paper, we evidence the complexation of above mentionned pollutants by cyclodextrins using high-resolution proton Nuclear Magnetic Resonance spectroscopy. The latter method is also used to afford a three-dimensional structure of inclusion complexes in solution and to show that cyclodextrins can as well discriminate between the optical isomers of synthetic geosmin and methyl-isoborneol. Finally, a solution to the problem of waste waters is proposed.
Tetrahedron-asymmetry | 1993
Eric Bonfand; Pascal Gosselin; Christian Maignan
Abstract Condensation of (R)-vinyl-p-tolylsulfoxide anion on carbonyl compounds led directly to chiral allylic sulfinylalcohols 1 . By treatment with NBS/Me 2 S, these alcohols 1 were converted into the rearranged primary allylic bromides 2 via SN 2 ′ displacement. Optically pure (R)- and (S)-2-p-tolylsulfinyl-1,3-alkadienes 3 resulted from the action of KOH/ROH upon these bromides 2 via E 2 ′ eliminations.
Tetrahedron-asymmetry | 1994
Pascal Gosselin; Eric Bonfand; Patricia Hayes; Richard Retoux; Christian Maignan
Abstract Reaction of (E)-(+)-(R)-2-p-tolylsulfinyl-1,3-pentadiene 1 with maleimide afforded 3 as a single, enantiomerically pure adduct under very mild conditions. 3 resulted from exclusive endo approach by a completely diastereofacialselective route. On the other hand, heterodiene (+)-(S)-3-p-tolylsulfinyl-3-buten-2-one 2 smoothly reacted with sensitive 2-methylenetetrahydrofuran yielding 1:1 diastereomeric dioxaspiroadducts 4a and 4b, readily separated by liquid chromatography.
Tetrahedron Letters | 1992
Eric Bonfand; Pascal Gosselin; Christian Maignan
Abstract The title compounds were readily prepared respectively from (S)-3-p-tolylsulfinylbut-3-en-2-ol 3 and (S)-3-p-tolylsulfinylbut-3-en-2-one 4.
Tetrahedron Letters | 1989
Pascal Gosselin; D. Joulain; P. Laurin; Francis Rouessac
Abstract The strongly earthy-smelling compound (±)-geosmin 1 is obtained stereospecifically in four steps and 42% overall yield from 1,4aβ-Dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 2 . The key step involves a one-pot double-reduction of an epoxytosylate.
Tetrahedron Letters | 1983
Pascal Gosselin; Francis Rouessac
Resume A synthesis of (±) aplysistatin 1 from geraniol is described in which the key step is the electrophilic cyclization of the bromohydrin 8 .
Tetrahedron Letters | 1986
Pascal Gosselin
Resume A new synthetic route to γ-damasoone 1 starting from methyl-γ-dithiocyclogeranate 2 is described. Addition of HMPT is found necessary to perform the reaction of allyllmagnesium bromide with dithioester 2 . A new, very mild hydrolysis method is developped in order to transform the resulting vinylsulfide 4 into 1 .
Tetrahedron Letters | 1982
Pascal Gosselin; Francis Rouessac
Abstract A new synthesis of 5-bromohexahydro-4,4,7a-trimethyl-2( 3H )-Benzofuranone (3aα,5β,7aβ)( 1 ) was achieved by electrophilic cyclization of the bromohydrin issued from pure homogeranic acid.
Tetrahedron-asymmetry | 2001
Pascal Gosselin; Martine Lelievre; Benedicte Poissonnier
Abstract The treatment of (+)- or (−)-fenchones epoxides with 1:2 85% H 3 PO 4 :DMSO for 30 min at 20°C induced an enantiospecific Wagner–Meerwein rearrangement affording new C(10)- O -substituted camphor derivatives which could prove useful as chiral auxiliaries.