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Accueil > Equipes de recherche > Nouvelles méthodes de synthèse pour l’interface chimie-biologie > Publications récentes

Publications récentes

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2018
  • Synthesis and Reactivity of Mixed Dimethylalkynylaluminum Reagents

    R. Piccardi, S. Turcaud, E. Benedetti, L. Micouin
    Synthesis, 2018, in press DOI: 10.1055/s-0037-1610392

    Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

  • Highly Enantioselective Desymmetrization of Centrosymmetric pseudo-para-Diformyl[2.2]paracyclophane via Asymmetric Transfer Hydrogenation

    M.-L. Delcourt, S. Simon, E. Benedetti, L.Micouin,
    ACS Catalysis, 2018, 8, 6612-6616

  • Rapid and Effective Synthesis of α-Acyloxy-α-alkynyltrimethylsilanes
    T. Zhao, R. Piccardi, L. Micouin.
    Org. Lett.., 2018,20, 5015-5018





2017
  • Synthesis and photophysical studies of through-space conjugated [2.2]paracyclophane-based naphthalene fluorophores

    E. Benedetti, M.-L. Delcourt, B. Gatin-Fraudet, S. Turcaud, L.Micouin,
    RSC Advances, 2017, 7, 50472-50476

  • Use of a redox probe for an electrochemical RNA–ligand binding assay in microliter droplets Guyon, H.; Mavré, F.; Catala, M.; Turcaud, S.; Brachet, F.; Limoges, B.; Tisné, C.; Micouin, L. Chem. Commun., 2017,53, 1140-1143

  • Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions Joosten, A.; Boultadaki-Arapinis, M.; Gandon, V.; Micouin, L.; Lecourt, T. J. Org. Chem. 2017, 82, 3291-3297

  • Modular access to N-substituted cis 5-amino-3-hydroxypiperidines
    Gordillo, P.; Clerici, P.; Micouin, L.
    J. Org. Chem. 2017, 82, 7689-7694.

Chapitres de livre

  • The Chemistry of Alkynylaluminum Species
    PATAI’S Chemistry of Functional Groups,

    Piccardi, R; Micouin, L.; Jackowski, O.
    Online 2009–2016 John Wiley & Sons, Ltd.
    DOI: 10.1002/9780470682531.pat0832, 2016


Edition d'ouvrages

  • Micouin, L; Marek I.; Rappoport, Z. The Chemistry of Organoaluminum Compounds PATAI's Chemistry of Functional Groups John Wiley & Sons Ltd, Chichester, 2017 ISBN: 978-1-119-02146-




2016

  • Expanding biohybrid-mediated asymmetric catalysis into the realm of RNA.
    Duchemin, N.; Benedetti, E.; Bethge, L.; Vonhoff, S.; Klussmann, S.; Vasseur, J. J.; Cossy, J.; Smietana, M.; Arseniyadis, S.
    Chem. Commun. 2016, 52, 8604.

  • Design, Synthesis and Binding Affinity Evaluation of New Hoechst 33258 Derivatives for the Development of Sequence-specific DNA-based Asymmetric Catalysts.
    Amirbekyan, K.; Duchemin, N.; Benedetti, E.; Joseph, R.; Colon, A.; Markarian, S.; Bethge, L.; Vonhoff, S.; Klussmann, S.; Cossy, J.; Vasseur, J.-J. ; Arseniyadis, S.; Smietana, M. ACS Catal. 2016, 6, 3096.

  • Efficient and scalable kinetic resolution of racemic 4-formyl[2,2]paracyclophane via asymmetric transfer hydrogenation Delcourt, M.-L.; Turcaud, S.; Benedetti, E.; Micouin, L. Adv. Synth. Catal. 2016, 358, 1213-1218

  • Continuous flow synthesis of dimethylalkynylaluminum reagents. Piccardi, R.; Coffinet, A.; Turcaud, S.; Benedetti, E.; Micouin, L. Synthesis, 2016, 48, 3272-3278

  • Rhodium(II)-Alkynyl Carbenoids Insertion into Si-H bonds: An Entry to Propargylic Geminal Bis(silanes) Courant, T.; Kumar, R; Turcaud, S; Micouin, L Org. Lett. 2016, 18, 4818-4820
Chapitres de livre

  • Synthesis of polyketides.
    Bressy, C.; Smietana, M.; Benedetti, E.; Arseniyadis S. in From Biosynthesis to Total Synthesis, (Ed. A.L. Zografos), Wiley 2016, Chapter 2, pp 44-86.

2015

  • DNA-cellulose: An economical, fully recyclable and highly effective chiral biomaterial for asymmetric catalysis.
    Benedetti, E.; Duchemin, N.; Bethge, L.; Vonhoff, S.; Klussmann, S.; Vasseur, J.-J.; Cossy, J.; Smietana, M.; Arseniyadis, S.
    Chem. Commun. 2015, 51, 6076 (Front Cover, Synfacts 2015, 11, 773).

  • Monitoring of reversible boronic acid-diol interactions by fluorine NMR spectroscopy in aqueous media Iannazzo, L. ; Benedetti, E ; Catala, M. ; Etheve-Quelquejeu, M. ; Tisné, C. ; Micouin, L. Org. Biomol. Chem. 2015, 13, 8817- 8821


Brevets:
  • Cyclic compounds having a 1,3 diamino-functionality for use in the treatment of HIV Infection,
    Corrot, E.; Blond, A.; Calvez, V. ; Marcellin, A.-G. ; Micouin, L. ; Soullié, C.
    EPCT/EP2015/062046 (WO 2015181387 A1) déposé le 29 mai 2015

  • Functionalized naphthalene fluorophores, Brummond, K. M.; Kocsis, L. S.; Benedetti, E.
    U.S. Patent No 9,133,234. Date de publication: 15/09/2015.

  • Synthesis, structure and use of functionalized naphthalenes, Brummond, K. M.; Kocsis, L. S.; Benedetti, E.
    U.S. Patent No 9,102,703. Date de publication: 11/08/2015.


2014

  • Recent Developments in Alkyne Borylations.
    Barberon, R.; Benedetti, E.; Vasseur, J.-J.; Cossy, J.; Arseniyadis, S.; Smietana, M.
    Tetrahedron 2014, 70, 843.

  • Electronic effects in Carbene-Mediated C-H Bond functionalization: An Experimental and Theoretical Study M. Boultadakis-Arapinis, M.; Gandon, V. ; Prost, E. ; Micouin, L. ; Lecourt, T. Adv. Synth. Catal. 2014, 356, 2493-2505

  • The design of RNA binders: targeting the HIV replication cycle as a case study, Blond, A.; Ennifar, E.; Tisné, C.; Micouin, L. ChemMedChem. 2014, 9, 1982-1996.

  • The reaction of dimethylalkynylaluminum reagents with trimethylsilyldiazomethane : original reactivity leading to new silylated alkynylhydrazones Kumar, R.; Turcaud, S. ; Micouin, L. Org. Lett. 2014, 16, 6192-6195


Brevets:
  • Cyclic compounds having a 1,3 diamino-functionality for use in the treatment of HIV Infection
    Blond, A.; Calvez, V. ; Marcellin, A.-G. ; Micouin, L. ; Soullié, C.
    EP14305808.9. déposé le 30 mai 2014


2013

  • Carbene-Mediated Functionalization of the Anomeric C-H Bond of Carbohydrates: Scope and Limitations Boultadakis Arapinis, M.; Prost, E.; Gandon, V.; Lemoine, P.; Turcaud, S.; Micouin, L.; Lecourt, T. Chem. Eur. J. 2013, 19, 6052-6066

  • Functionalization of the anomeric C–H bond of carbohydrates: old strategies and new opportunities Boultadakis Arapinis, M. ; Lescot, C. ; Turcaud, S. ; Micouin, L. ; Lecourt, T. Synlett 2013, 2477-2491

  • Modular access to N-substituted cis-3,5-diaminopiperidines Blond, A.; Dockerty, P; Álvarez, R.; Turcaud, S.; Lecourt, T.; Micouin, L. J. Org. Chem. 2013, 78, 12226-12242

  • Synthesis and biological evaluation of a new derivative of bevirimat that targets the Gag CA-SP1 cleavage site. Coric, P; Turcaud, S; Souquet, F; Briant, L; Gay, B; Royer, J; Chazal, N; Bouaziz, S European Journal of Medicinal Chemistry 2013, 62, 453-465

  • The reactivity of the diethyl α-acylphosphonates with the various α-aminoesters: synthesis and DFT (density functional theory) study Mellah, I; Turcaud, S; Ayadi, S Journal of Chemical and Pharmaceutical Research 2013, 5, 928-932
Chapitre de livre:

  • Carbon-Carbon Bond Forming Reactions Mediated by Organomagnesium Reagents Metal-Catalyzed Single Bond Construction
    Chemla, F. Ferreira, F.; Jackowski, O.; Micouin, L.; Pérez-Luna, A., de Meijere A.; Bräse, S.; Oestreich M. Wiley-VCH, 2013, 365-422

  • Carbon-Carbon Bond Forming Reactions Mediated by Organozinc Reagents Metal-Catalyzed Single Bond Construction
    Chemla, F. Ferreira, F.; Jackowski, O.; Micouin, L.; Pérez-Luna, A., de Meijere A.; Bräse, S.; Oestreich M. Wiley-VCH, 2013, 279-364

Brevets:
  • Preparation of derivatives of 3-O-(3',3'-dimethylsuccinyl)-betulinic acid for the treatment of HIV.
    Bouaziz, S; Coric, P; Boulanger, P; Hong, Saw-See; Turcaud, S
    Eur. Pat. Appl. (2013), EP 2567965 A1 20130313

2012
  • Fragment-based design of small RNA binders: promising developments and contribution of NMR. Moumné, R.; Catala, M.; Larue, V.; Micouin, L.; Tisné, C. Biochimie 2012, 94, 1607-1619

  • Investigation of RNA-ligand interaction by 19F NMR spectroscopy using fluorinated probes. Lombès, T. ; Moumné, R. ; Larue, V. ; Prost, E. ; Catala, M.; Lecourt, T.; Dardel, F.; Micouin, L. ; Tisné, C. Angew. Chem. Int. Ed. 2012, 51, 9530-9534

  • Gram-Scale Quaternarization of the Anomeric Position of Carbohydrates: Dramatic Effects of Molecular Sieves on Rh(II)-Mediated Decomposition of Diazo sugars. Boultadakis Arapinis, M.; Lescot, C. ; Micouin, L. ; Lecourt, T. Synthesis 2012, 44, 3731-3734
Chapitre de livre:

  • Recent developments in the synthesis 1,4,5-trisubstituted triazoles

    Mignani, S.; Zhou, Y.; Lecourt, T.; Micouin, L.
    Topics in Heterocyclic Chemistry, 2012, Vol. 28, 185-232

  • 2,3-Diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic Acid, 2,3-Diethyl Ester
    Bhanu Prasad, B. A. ; Gilbertson, S. R. ; Lombès, T. ; Micouin, L.
    eEROS, John Wiley & Sons, UK, 2012 DOI: 10.1002/047084289X.rn01437

2011
  • Rhodium(II) carbene-mediated modification of 2-deoxystreptamine surrogates. A. Blond, R. Moumné, G. Bégis, M. Pasco, T. Lecourt, L. Micouin Tetrahedron Lett. 2011, 52, 3201-3203.

  • Stereoselective synthesis of fluorinated 1,3-cis-diaminocyclopentanes. M. Pasco, R. Moumné, T. Lecourt, L. Micouin J. Org. Chem. 2011, 76, 5237-5142.

  • Chemodivergent synthesis of 7-Aryl/alkyl-6-hydroxy-1,4-oxazepan-5-ones and 2-[Aryl/alkyl(hydroxy)methyl]morpholin-3-ones from a common epoxyamide precursor. D. M. Apraicio, J. L. Teran, L. F. Roa, D. Gnesso, J. R. Juarez, M. L. Orea, A. Mendoza, M. Flores-Alamo, L. Micouin Synthesis, 2011, 2310-2320.

  • Rh(II) Carbene-Mediated Synthesis of Methyl α- and β-Ketopyranosides: Preparation of Carbene Precursors, Quaternarization of the Anomeric Position, and Ring Opening of γ-Lactone. M. Boultadakis-Arapinis, C. Lescot, L. Micouin, T. Lecourt Journal of Carbohydrate Chemistry, 2011, 30:7-9, 587-604.

  • Direct Synthesis of Polysubstituted Aluminoisoxazoles and Pyrazoles by a Metalative Cyclization. O. Jackowski, T. Lecourt, L. Micouin Org. Lett., 2011, 13, 5664-5667




2010

  • Tether influence on the binding properties of tRNALys3 ligands designed by a fragment based approach. R. Moumné, V. Larue, B. Seijo, T. Lecourt, L. Micouin and C. Tisné, Org. Biomol. Chem. 2010, 8, 1154-1159

  • Copper-Catalyzed Ring-Opening of Polycyclic Hydrazines With Trialkylaluminium Reagents and SimplePhos Ligands. L. Palais, C. Bournaud, L. Micouin, A. Alexakis, Chem. Eur. J. 2010, 16, 2567-2573.

  • Direct Synthesis of 1,4-Disubstituted-5-alumino-1,2,3-triazoles By a Copper-Catalyzed Cycloaddition of Organic Azides and Mixed-Aluminum acetylides. Y. Zhou, T. Lecourt, L. Micouin, Angew. Chem. Int. Ed. 2010, 49, 2607-2610.

  • Fluorinated Diaminocyclopentanes as Chiral Sensitive NMR Probes of RNA Structure. R. Moumné, M. Pasco, E. Prost, T. Lecourt, L. Micouin, C. Tisné, J. Am. Chem. Soc. 2010, 132, 13111-13113.

  • Rh(II) carbene-promoted activation of the anomeric C-H bond of carbohydrates: a stereospecific entry towards α- and β-ketopyranosides. M. Boultadakis-Arapinis, P. Lemoine, S. Turcaud, L. Micouin, T. Lecourt, J. Am. Chem. Soc. 2010, 132, 15477-15479.

2009

2008

2007


2006