dbCGE Equipes : Equipe A116 – Laboratoire de Synthèse et réactivité organique (ULP)

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dbCGE > Equipes > Equipe A116 – Laboratoire de Synthèse et réactivité organique (ULP)

  • Université de Strasbourg, Institut de Chimie

Activités de Recherches

dot-2709229 Méthodes en synthèse

  • Synthèse de composés de type enyne
  • Synthèse d’époxydes fonctionnalisés
  • Synthèse de cycles et d’hétérocycles fonctionnalisés

dot-2709229 Synthèse de produits naturels

  • Synthèse totale d’antibiotiques anticancéreux de type enediyne
  • Synthèse totale de composés d’origine marine de type eicosanoide
  • Synthèse de glycopeptides et de sucres fluorés

dot-2709229 Synthèse asymétrique

  • copules chirales à base de sucres
  • catalyseurs chiraux à base de sucres
Membres de l’équipe
  • Mira AL LAKKIS
  • Patrick PALE
2007 – INHIBAP-N (porteur : Céline TARNUS)
Nouvelle famille de molécules inhibitrices de l’AP-N ou CD13, enzyme intervenant dans le processus d’angiogénèse des tumeurs cancéreuses
2005 – PNES Poumon (porteur : )
PNES Poumon
2005 – PNES Rein (porteur : )
PNES Rein
Collaborations
Publications
  • Kern N, Felten AS, Weibel JM, Pale P, Blanc A. Robust synthesis of N-sulfonylazetidine building blocks via ring contraction of alpha-bromo N-sulfonylpyrrolidinones. Org Lett. 2014 Dec 5;16(23):6104-7. doi: 10.1021/ol5029496. Epub 2014 Nov 14.
  • Jacques B, Hueber D, Hameury S, Braunstein P, Pale P, Blanc A, de Fremont P. Synthesis, Characterization, and Catalytic Activity of Alcohol-Functionalized NHC Gold(I/III) Complexes. Organometallics. 2014 May 12;33(9):2326-35.
  • Hueber D, Hoffmann M, Louis B, Pale P, Blanc A. Inorganic-organic heteropolyacid-gold(I) hybrids: structures and catalytic applications. Chemistry. 2014 Apr 1;20(14):3903-7. doi: 10.1002/chem.201304680. Epub 2014 Feb 26.
  • Hoffmann M, Weibel JM, de Fremont P, Pale P, Blanc A. Gold(I)/(III)-catalyzed rearrangement of divinyl ketones and acyloxyalkynyloxiranes into cyclopentenones. Org Lett. 2014 Feb 7;16(3):908-11. doi: 10.1021/ol403663j. Epub 2014 Jan 23.
  • Bernardon C, Louis B, Beneteau V, Pale P. Diels-Alder Reaction between Isoprene and Methyl Acrylate over Different Zeolites: Influence of Pore Topology and Acidity. Chempluschem. 2013 Sep;78(9):1134-41.
  • Orbisaglia S, Jacques B, Braunstein P, Hueber D, Pale P, Blanc A, de Fremont P. Synthesis, Characterization, and Catalytic Activity of Cationic NHC Gold(III) Pyridine Complexes. Organometallics. 2013 Aug 12;32(15):4153-64.
  • Mendonca GF, Bastos AR, Boltz M, Louis B, Pale P, Esteves PM, de Mattos MCS. Electrophilic chlorination of arenes with trichloroisocyanuric acid over acid zeolites. Appl Catal A-gen. 2013 Jun 10;460:46-51.
  • Cheval NP, Dikova A, Blanc A, Weibel JM, Pale P. Vinyl nosylates: an ideal partner for palladium-catalyzed cross-coupling reactions. Chemistry. 2013 Jul 1;19(27):8765-8. doi: 10.1002/chem.201300127. Epub 2013 May 21.
  • Kern N, Hoffmann M, Blanc A, Weibel JM, Pale P. Gold(I)-catalyzed rearrangement of N-aryl 2-alkynylazetidines to pyrrolo[1,2-a]indoles. Org Lett. 2013 Feb 15;15(4):836-9. doi: 10.1021/ol303518n. Epub 2013 Jan 25.
  • Borghese S, Drouhin P, Beneteau V, Louis B, Pale P. Silver-zeolite catalysed solvent free synthesis of (spiro)ketals. Green Chem. 2013;15(6):1496-500.
  • Genelot M, Cheval NP, Vitorino M, Berrier E, Weibel JM, Pale P, Mortreux A, Gauvin RM. Well-defined silica-supported molybdenum nitride species: silica grafting triggers alkyne metathesis activity. Chem Sci. 2013;4(6):2680-5.
  • Hoffmann M, Miaskiewicz S, Weibel JM, Pale P, Blanc A. Gold(I)-catalyzed formation of furans from gamma-acyloxyalkynyl ketones. Beilstein J Org Chem. 2013 Aug 30;9:1774-80. doi: 10.3762/bjoc.9.206.
  • Boltz M, de Mattos MCS, Esteves PM, Pale P, Louis B. Green route for the chlorination of nitrobenzene. Appl Catal A-gen. 2012 Dec 27;449:1-8.
  • Chassaing S, Specklin S, Weibel JM, Pale P. Vinyl and Aryl Sulfonates: Preparations and Applications in Total Synthesis. Curr Org Synth. 2012 Dec;9(6):806-27.
  • Kern N, Dombray T, Blanc A, Weibel JM, Pale P. Silver(I)-catalyzed deprotection of p-methoxybenzyl ethers: a mild and chemoselective method. J Org Chem. 2012 Oct 19;77(20):9227-35. doi: 10.1021/jo301787v. Epub 2012 Oct 9.
  • Chassaing S, Specklin S, Weibel JM, Pale P. Vinyl triflates derived from 1,3-dicarbonyl compounds and analogs: access and applications to organic synthesis. . 2012 Sep 9;68(36):7245-73.
  • Olmos A, Rigolet S, Louis B, Pale P. Design of Scandium-Doped USY Zeolite: An Efficient and Green Catalyst for Aza-Diels-Alder Reaction. . 2012 Jun 28;116(25):13661-70.
  • Kern N, Blanc A, Miaskiewicz S, Robinette M, Weibel JM, Pale P. Coinage metals-catalyzed cascade reactions of aryl alkynylaziridines: silver(I)-single vs gold(I)-double cyclizations. J Org Chem. 2012 May 4;77(9):4323-41. Epub 2012 Apr 15.
  • Olmos A, Louis B, Pale P. Scandium(III)-zeolites as new heterogeneous catalysts for imino-Diels-Alder reactions. Chemistry. 2012 Apr 16;18(16):4894-901. doi: 10.1002/chem.201103624. Epub 2012
  • Specklin S, Gallier F, Mezaache R, Harkat H, Dembele YA, Weibel JM, Blanc A, Pale P. Copper(II) bromide as efficient catalyst for silyl- to bisarylmethyl ethers interconversion (transprotection). . 2011 Nov 2;52(44):5820-3.
  • Louis B, Laugel G, Pale P, Pereira MM. Rational Design of Microporous and Mesoporous Solids for Catalysis: From the Molecule to the Reactor. . 2011 Aug;3(8):1263-72.
  • Kern N, Blanc A, Weibel JM, Pale P. Gold(I)-catalyzed rearrangement of aryl alkynylaziridines to spiro[isochroman-4,2′-pyrrolines]. Chem Commun (Camb). 2011 Jun 21;47(23):6665-7. Epub 2011 May 5.
  • Boltz M, Blanc A, Laugel G, Pale P, Louis B. Heterogenization of [Cu(2,2 ‘-bpy)Cl-2] and [Cu(1,10-phen)Cl-2] on Polyoxometalates: New Catalysts for the Selective Oxidation of Tetralin. . 2011 May;32(5):807-11.
  • Olmos A, Sommer J, Pale P. Scandium(III) zeolites as new heterogeneous catalysts: [4+2]cyclocondensation of in situ generated aryl imines with alkenes. Chemistry. 2011 Feb 7;17(6):1907-14. doi: 10.1002/chem.201002649. Epub
  • Albrecht S, Al-Lakkis-Wehbe M, Orsini A, Defoin A, Pale P, Salomon E, Tarnus C, Weibel JM. Amino-benzosuberone: a novel warhead for selective inhibition of human aminopeptidase-N/CD13. Bioorg Med Chem. 2011 Feb 15;19(4):1434-49. Epub 2011 Jan 11.
  • Borghese S, Blanc A, Pale P, Louis B. Bronsted acid sites in metal-containing solid acids: from quantification to molecular design of new catalysts/silver(I)-polyoxometalates. Dalton Trans. 2011 Feb 14;40(6):1220-3. Epub 2011 Jan 6.
  • Borghese S, Louis B, Blanc A, Pale P. Design of silver(I)-heteropolyacids: toward the molecular control of reactivity in organic chemistry. . 2011;1(6):981-6.
  • Dombray T, Blanc A, Weibel JM, Pale P. Gold(I)-catalyzed cycloisomerization of beta-alkynylpropiolactones to substituted alpha-pyrones. Org Lett. 2010 Dec 3;12(23):5362-5. Epub 2010 Nov 11.
  • Boningari T, Olmos A, Reddy BM, Sommer J, Pale P. Zeo-Click Chemistry: Copper(I)-Zeolite-Catalyzed Cascade Reaction; One-Pot Epoxide Ring-Opening and Cycloaddition. Eur J Org Chem. 2010 Nov;33:6338-47.
  • Beneteau V, Olmos A, Boningari T, Sommer J, Pale P. Zeo-click synthesis: Cu-I-zeolite-catalyzed one-pot two-step synthesis of triazoles from halides and related compounds Tetrahedron Lett. 2010 Jul 14;51(28):3673-7
  • Chassaing S, Alix A, Olmos A, Keller M, Sommer J, Pale P. Metal-doped Zeolites as Green Catalysts for Organic Synthesis Znaturforsch(b). 2010 Jul;65(7):783-90
  • Chassaing S, Alix A, Boningari T, Sido KSS, Keller M, Kuhn P, Louis B, Sommer J, Pale P. Copper(I)-Zeolites as New Heterogeneous and Green Catalysts for Organic Synthesis Synthesis. 2010 May;9:1557-67
  • Besbes N, Jellali H, Pale P, Srasra E, Efrit ML. Transformations of N-acylaziridines catalysed by support-based silica and alumina: Mechanistic elucidation. C R Chim. 2010 Mar;13(3):358-64.
  • Blanc A, Alix A, Weibel JM, Pale P. Gold(I)-Catalyzed Tandem Rearrangement-Nucleophilic Substitution of alpha-Acetoxy Alkynyl Oxiranes or Aziridines: Efficient Approach to Furans and Pyrroles Eur J Org Chem. 2010 Mar;9:1644-7
  • Besbes N, Jellali H, Pale P, Efrit ML, Srasra E. Isomerisation Catalysee Par le Gel de Silice et L’argile Activee de N-Acyl-2,2-Dimethylaziridines: Approche Mecanistique Phosphorus Sulfur Silicon Relat Elem. 2010;185(4):883-9
  • Mezaache R, Dembele YA, Bikard Y, Weibel JM, Blanc A, Pale P. Copper(II) bromide as an efficient catalyst for the selective protection and deprotection of alcohols as bis(4-methoxyphenyl)methyl ethers Tetrahedron Lett. 2009 Dec 30;50(52):7322-6
  • Olmos A, Alix A, Sommer J, Pale P. Sc(III)-doped zeolites as new heterogeneous catalysts: mukaiyama aldol reaction. Chemistry. 2009 Oct 26;15(42):11229-34.
  • Blanc A, Tenbrink K, Weibel JM, Pale P. Mechanistic studies and improvement of coinage metal-catalyzed transformation of alkynyloxiranes to furans: an alcohol addition-cyclization-elimination cascade. J Org Chem. 2009 Aug 7;74(15):5342-8.
  • Blanc A, Tenbrink K, Weibel JM, Pale P. Silver(I)-catalyzed cascade: direct access to furans from alkynyloxiranes. J Org Chem. 2009 Jun 5;74(11):4360-3.
  • Harkat H, Dembele AY, Weibel JM, Blanc A, Pale P. Cyclization of alkynoic acids with gold catalysts: a surprising dichotomy between Au-I and Au-III Tetrahedron. 2009 Feb 28;65(9):1871-9
  • Kuhn P, Pale P, Sommer J, Louis B. Probing Cu-USY Zeolite Reactivity: Design of a Green Catalyst for the Synthesis of Diynes J Phys Chem C. 2009 Feb 19;113(7):2903-10
  • Keller M, Sido AS, Pale P, Sommer J. Copper(I) zeolites as heterogeneous and ligand-free catalysts: [3+2] cycloaddition of azomethine imines. Chemistry. 2009;15(12):2810-7.
  • Fecourt F, Carlier C, Pale P. Rapid Synthesis of Taxifolione and Taxifolial D, Two Metabolites from the Marine Alga Caulerpa taxifolia Lett Org Chem. 2009 Jan;6(1):65-70
  • Kuhn P, Alix A, Kumarrajaa M, Louis B, Pale P, Sommer J. Copper-Zeolites as Catalysts for the Coupling of Terminal Alkynes: An Efficient Synthesis of Diynes Eur J Org Chem. 2009 Jan;3:423-9
  • Bikard Y, Mezaache R, Weibel JM, Benkouider A, Sirlin C, Pale P. Diarylmethyl ethers and Pd salts or complexes: a perfect combination for the protection and deprotection of alcohols Tetrahedron. 2008 Oct 27;64(44):10224-32
  • Specklin S, Bertus P, Weibel JM, Pale P. A versatile and highly stereoselective access to vinyl triflates derived from 1,3-dicarbonyl and related compounds. J Org Chem. 2008 Oct 3;73(19):7845-8. Epub 2008 Sep 4.
  • Besbes N, Ayed T, Pale P, Tangour B. Thermal rearrangement of substituted N-acyl-2,2-dimethyl aziridines: a mechanistic study C R Chim. 2008 Oct;11(10):1283-8
  • Alix A, Chassaing S, Pale P, Sommer J. ‘Click chemistry’ in Cu-I-zeolites: a convenient access to glycoconjugates Tetrahedron. 2008 Sep 8;64(37):8922-9
  • Patil MK, Keller M, Reddy BM, Pale P, Sommer J. Copper zeolites as green catalysts for multicomponent reactions of aldehydes, terminal alkynes and amines: An efficient and green synthesis of propargylamines Eur J Org Chem. 2008 Sep;26:4440-5
  • Weibel JM, Blanc A, Pale P. Ag-mediated reactions: Coupling and heterocyclization reactions Chem Rev. 2008 Aug;108(8):3149-73. Epub 2008 Jul 11. – Review
  • Cordonnier MC, Blanc A, Pale P. Gold(I)-catalyzed rearrangement of alkynyloxiranes: A mild access to divinyl ketones Org Lett. 2008 Apr 17;10(8):1569-72. Epub 2008 Mar 22.
  • Sani-Souna-Sido A, Chassaing S, Pale P, Sommer J. Behavior of arylvinylketones in zeolites: A systematic study Appl Catal A-gen. 2008 Mar 1;336(1-2):101-8
  • Harkat H, Blanc A, Weibel JM, Pale P. Versatile and expeditious synthesis of aurones via Au-I-catalyzed cyclization J Org Chem. 2008 Feb 15;73(4):1620-3. Epub 2008 Jan 15.
  • Chassaing S, Sido ASS, Alix A, Kumarraja M, Pale P, Sommer J. “Click Chemistry” in zeolites: Copper(I) zeolites as new heterogeneous and ligand-free catalysts for the Huisgen [3+2] cycloaddition Chemistry. 2008;14(22):6713-21.
  • Bikard Y, Weibel JM, Sirlin C, Dupuis L, Loeffler JP, Pale P. PdCl2, a useful catalyst for protection of alcohols as diphenylmethyl (DPM) ethers Tetrahedron Lett. 2007 Dec 10;48(50):8895-9
  • Vasilyev AV, Walspurger S, Chassaing S, Pale P, Sommer J. One-step addition of sulfonic acids to acetylene derivatives: An alternative and stereoselective approach to vinyl triflates and fluorosulfonates Eur J Org Chem. 2007 Dec;34:5740-8
  • Aberkane MC, Dibi A, Haba H, Benkhaled M, Benkouider A, Mokhtari M, Mosset P, Pale P. Guaianolide and pseudoguaianolide from Pulicaria laciniata Asian J Chem. 2007 Nov;19(6):4954-6.
  • Bodlenner A, Alix A, Weibel JM, Pale P, Ennifar E, Paillart JC, Walter P, Marquet R, Dumas P. Synthesis of a neamine dimer targeting the dimerization initiation site of HIV-1 RNA. Org Lett. 2007 Oct 25;9(22):4415-8. Epub 2007 Oct 4.
  • Ennifar E, Paillart JC, Bernacchi S, Walter P, Pale P, Decout JL, Marquet R, Dumas P. A structure-based approach for targeting the HIV-1 genomic RNA dimerization initiation site. Biochimie. 2007 Oct;89(10):1195-203. Epub 2007 Mar 12. – Review
  • Chassaing S, Kumarraja M, Pale P, Sommer J. Zeolite-directed cascade reactions: cycliacyarylation versus decarboxyarylation of alpha,beta-unsaturated carboxylic acids. Org Lett. 2007 Sep 27;9(20):3889-92. Epub 2007 Sep 6.
  • Sido ASS, Chassaing S, Kumarraja M, Pale P, Sommer J. Solvent-dependent behavior of arylvinylketones in HUSY-zeolite: a green alternative to liquid superacid medium Tetrahedron Lett. 2007 Aug 13;48(33):5911-4
  • Halbes-Letinois U, Weibel JM, Pale P. The organic chemistry of silver acetylides. Chem Soc Rev. 2007 May;36(5):759-69. Epub 2007 Jan 23.
  • Chassaing S, Kumarraja M, Souna Sido AS, Pale P, Sommer J. Click chemistry in CuI-zeolites: the Huisgen [3 + 2]-cycloaddition. Org Lett. 2007 Mar 1;9(5):883-6. Epub 2007 Feb 8.
  • Harkat H, Weibel JM, Pale P. Synthesis of functionalized THF and THP through Au-catalyzed cyclization of acetylenic alcohols Tetrahedron Lett. 2007 Feb 19;48(8):1439-42.
  • Harkat H, Weibel JM, Pale P. A mild access to gamma- or delta-alkylidene lactones through gold catalysis. Tetrahedron Lett. 2006 Aug 28;47(35):6273-6.
  • Viterisi A, Orsini A, Weibel JM, Pale P. A mild access to silver acetylides from trimethylsilyl acetylenes. Tetrahedron Lett. 2006 Apr 17;47(16):2779-81.
  • Ennifar E, Paillart JC, Bodlenner A, Walter P, Weibel JM, Aubertin AM, Pale P, Dumas P, Marquet R. Targeting the dimerization initiation site of HIV-1 RNA with aminoglycosides: from crystal to cell. Nucleic Acids Res. 2006 May 5;34(8):2328-39. Print 2006.
  • Letinois-Halbes U, Pale P, Berger S. Ag NMR as a tool for mechanistic studies of Ag-catalyzed reactions: evidence for in situ formation of alkyn-1-yl silver from alkynes and silver salts. J Org Chem. 2005 Nov 11;70(23):9185-90.
  • Walspurger S, Vasil’ev AV, Sommer J, Pale P, Savechenkov PY, Rudenko AP. Protonation of 3-arylpropynoic acid derivatives in superacids. Russ J Organ Chem. 2005 Oct;41(10):1485-92.
  • Halbes-Letinois U, Vasiliev A, Pale P. Regio- and chemoselective coupling of polyalkynes: A convenient access to polyarylacetylenes and polyenynes. Eur J Org Chem. 2005 Jun 27;13:2828-34.
  • Walspurger S, Vasilyev AV, Sommer J, Pale P. Chemistry of 3-arylindenones: behavior in superacids and photodimerization. Tetrahedron. 2005 Apr 4;61(14):3559-64.
  • Vasil’ev AV, Walspurger S, Pale P, Sommer J. [2+2]-photodimerization of 3-arylindenones. Russ J Organ Chem. 2005 Apr;41(4):618-9.
  • Orsini A, Viterisi A, Bodlenner A, Weibel JM, Pale P. A chemoselective deprotection of trimethylsilyl acetylenes catalyzed by silver salts. Tetrahedron Lett. 2005 Mar 28;46(13):2259-62.
  • Maiereanu C, Kanai A, Weibel JM, Pale P. Synthesis of 2-deoxy-2-thiophenylglucosyl azides through 1,2 thio migration of thiophenyl mannosides. J Carbohydr Chem. 2005;24(8-9):831-42.