Gwilherm Evano

Summary

Country: France

Publications

  1. ncbi request reprint 3-Aminopyrrolidines via ring rearrangement of 2-aminomethylazetidines. Synthesis of (-)-absouline
    Monica Vargas-Sanchez
    Laboratoire SIRCOB, UMR CNRS 8086, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 7:5861-4. 2005
  2. doi request reprint Copper-mediated cross-coupling of 1,1-dibromo-1-alkenes with dialkyl phosphites: a convenient synthesis of 1-alkenylphosphonates
    Gwilherm Evano
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Chem Commun (Camb) 47:179-81. 2011
  3. ncbi request reprint Ynamides: versatile tools in organic synthesis
    Gwilherm Evano
    Institut Lavoisier de Versailles, UMR CNRS, Universite de Versailles Saint Quentin en Yvelines, France
    Angew Chem Int Ed Engl 49:2840-59. 2010
  4. doi request reprint Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis
    Gwilherm Evano
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    Chem Rev 108:3054-131. 2008
  5. doi request reprint Copper-catalyzed cyclization of iodo-tryptophans: a straightforward synthesis of pyrroloindoles
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 10:3841-4. 2008
  6. doi request reprint Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 11:4454-7. 2009
  7. doi request reprint Total synthesis of chaetominine
    Mathieu Toumi
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 10:5027-30. 2008
  8. ncbi request reprint Exploring the anionic reactivity of ynimines, useful precursors of metalated ketenimines
    Anouar Laouiti
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 16:2252-5. 2014
  9. ncbi request reprint A convergent synthesis of the fully elaborated macrocyclic core of TMC-95A
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 16:1306-9. 2014
  10. doi request reprint Total synthesis of the cyclopeptide alkaloid paliurine E. insights into macrocyclization by ene--enamide RCM
    Mathieu Toumi
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    J Org Chem 73:1270-81. 2008

Collaborators

  • Ganesan Karthikeyan
  • Nicolas Blanchard
  • Karen Wright
  • Anders A Jensen
  • Francois Couty
  • Alexis Coste
  • Mathieu Toumi
  • Wafa Gati
  • Jérôme Marrot
  • Mohamed B Rammah
  • Mohamed M Rammah
  • Anouar Laouiti
  • Kevin Jouvin
  • Taoufik Boubaker
  • Alexandre Bayle
  • Monica Vargas-Sanchez
  • Hans Brauner-Osborne
  • Cédric Theunissen
  • Romain Veillard
  • Carole Alayrac
  • Annie Claude Gaumont
  • Frédéric Legrand
  • Vanessa Razafimahaléo
  • Gloria Bouzas
  • Mie Kusk
  • Nathalie Chopin
  • Birgitte Nielsen
  • Nicolas Rabasso
  • Lennart Bunch
  • Damien Prim

Detail Information

Publications22

  1. ncbi request reprint 3-Aminopyrrolidines via ring rearrangement of 2-aminomethylazetidines. Synthesis of (-)-absouline
    Monica Vargas-Sanchez
    Laboratoire SIRCOB, UMR CNRS 8086, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 7:5861-4. 2005
    ..A concise stereocontrolled synthesis of (-)-absouline was achieved on the basis of this new method...
  2. doi request reprint Copper-mediated cross-coupling of 1,1-dibromo-1-alkenes with dialkyl phosphites: a convenient synthesis of 1-alkenylphosphonates
    Gwilherm Evano
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Chem Commun (Camb) 47:179-81. 2011
    ..The reaction allows for formal substitution of both bromine atoms, respectively, by an hydrogen and a dialkoxyphosphoryl...
  3. ncbi request reprint Ynamides: versatile tools in organic synthesis
    Gwilherm Evano
    Institut Lavoisier de Versailles, UMR CNRS, Universite de Versailles Saint Quentin en Yvelines, France
    Angew Chem Int Ed Engl 49:2840-59. 2010
    ..This Review highlights major developments in this area...
  4. doi request reprint Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis
    Gwilherm Evano
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    Chem Rev 108:3054-131. 2008
  5. doi request reprint Copper-catalyzed cyclization of iodo-tryptophans: a straightforward synthesis of pyrroloindoles
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 10:3841-4. 2008
    ..Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems...
  6. doi request reprint Synthesis of ketene N,N-acetals by copper-catalyzed double-amidation of 1,1-dibromo-1-alkenes
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 11:4454-7. 2009
    ..The reaction was found to proceed through a regioselective monocoupling reaction followed by dehydrobromination and hydroamidation...
  7. doi request reprint Total synthesis of chaetominine
    Mathieu Toumi
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 10:5027-30. 2008
    ..This effort also documents the first example of an oxidative rearrangement yielding to homochiral spirocyclic pyrrolidinyloxindoles...
  8. ncbi request reprint Exploring the anionic reactivity of ynimines, useful precursors of metalated ketenimines
    Anouar Laouiti
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 16:2252-5. 2014
    ..The metalated ketenimines can then be trapped with various electrophiles and, depending on their substitution pattern, afford original and divergent entries to various building blocks. ..
  9. ncbi request reprint A convergent synthesis of the fully elaborated macrocyclic core of TMC-95A
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 16:1306-9. 2014
    ..A highly efficient organocatalyzed aldolization between isatin and dihydroxyacetone derivatives and formation of the biaryl subunit with concomitant macrocyclization are the characteristic features of this synthesis. ..
  10. doi request reprint Total synthesis of the cyclopeptide alkaloid paliurine E. insights into macrocyclization by ene--enamide RCM
    Mathieu Toumi
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    J Org Chem 73:1270-81. 2008
    ..Further insights on the macrocyclization by ene--enamide RCM are also discussed...
  11. ncbi request reprint Total synthesis of the cyclopeptide alkaloid abyssenine A. Application of inter- and intramolecular copper-mediated coupling reactions in organic synthesis
    Mathieu Toumi
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 78035, Versailles Cedex, France
    J Org Chem 72:9003-9. 2007
    ..The synthetic utility of copper-catalyzed coupling reactions was further demonstrated to install the enamide with a concomitant straightforward macrocyclization starting from acyclic alpha-amido-omega-vinyl iodide 13...
  12. ncbi request reprint Copper-mediated coupling of 1,1-dibromo-1-alkenes with nitrogen nucleophiles: a general method for the synthesis of ynamides
    Alexis Coste
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Angew Chem Int Ed Engl 48:4381-5. 2009
    ....
  13. doi request reprint Intramolecular carbocupration of N-aryl-ynamides: a modular indole synthesis
    Wafa Gati
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France, Laboratoire de Chimie Hétérocyclique, Produits Naturels et Réactivité, Departement de Chimie, Faculte des Sciences de Monastir, Universite de Monastir, Avenue de l Environnement, 5019 Monastir, Tunisia, and Laboratoire de Chimie Organique, Service de Chimie et PhysicoChimie Organiques, Universite Libre de Bruxelles, avenue F D Roosevelt 50, CP160 06, 1050 Brussels, Belgium
    Org Lett 15:3122-5. 2013
    ..This further extends the synthetic utility of ynamides in organic synthesis and provides additional insights on the use of intramolecular carbometalation reactions. ..
  14. doi request reprint De novo synthesis of 1,4-dihydropyridines and pyridines
    Wafa Gati
    Institut Lavoisier de Versailles, UMR CNRS, Universite de Versailles Saint Quentin en Yvelines, France
    J Am Chem Soc 134:9078-81. 2012
    ..This procedure provides an efficient, divergent, and straightforward entry to a wide range of polysubstituted dihydropyridines and pyridines starting from readily available N-allyl-ynamides...
  15. ncbi request reprint Total synthesis of paliurine F
    Mathieu Toumi
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45 Avenue des Etats Unis, 78035 Versailles Cedex, France
    Angew Chem Int Ed Engl 46:572-5. 2007
  16. pmc Intramolecular carbolithiation of N-allyl-ynamides: an efficient entry to 1,4-dihydropyridines and pyridines - application to a formal synthesis of sarizotan
    Wafa Gati
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France Laboratoire de Chimie Organique Hétérocyclique LCOH LCOHSNR LR11ES39, Departement de Chimie, Faculte des Sciences de Monastir, Universite de Monastir, Avenue de l Environnement, 5019 Monastir, Tunisia
    Beilstein J Org Chem 8:2214-22. 2012
    ....
  17. ncbi request reprint Copper-catalyzed oxidative alkynylation of diaryl imines with terminal alkynes: a facile synthesis of ynimines
    Anouar Laouiti
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 14:6-9. 2012
    ..An improved copper-catalyzed oxidative dimerization of imines to azines and the synthesis of dienes and azadienes from ynimines are also described...
  18. ncbi request reprint Practical asymmetric preparation of azetidine-2-carboxylic acid
    Francois Couty
    Laboratoire SIRCOB, UMR CNRS 8086, Universite de Versailles Saint Quentin en Yvelines, France
    J Org Chem 70:9028-31. 2005
    ..Synthetic highlights include the construction of the azetidine ring using an intramolecular alkylation and the use of optically active alpha-methylbenzylamine as chiral auxiliary...
  19. doi request reprint Unprecedented synthesis of alkynylphosphine-boranes through room-temperature oxidative alkynylation
    Kevin Jouvin
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 15:4592-5. 2013
    ..The reaction, which proceeds at room temperature, is applicable to the preparation of enantioenriched and structurally complex alkynylphosphine-boranes. ..
  20. ncbi request reprint Copper-catalyzed coupling of 1,1-dibromo-1-alkenes with phenols: a general, modular, and efficient synthesis of ynol ethers, bromo enol ethers, and ketene acetals
    Kevin Jouvin
    Institut Lavoisier de Versailles, UMR CNRS 8180, Universite de Versailles Saint Quentin en Yvelines, 45, Avenue des Etats Unis, 78035 Versailles Cedex, France
    Org Lett 14:1652-5. 2012
    ....
  21. ncbi request reprint A convergent synthesis of the macrocyclic core of cytotrienins: application of RCM for macrocyclization
    Gwilherm Evano
    Department of Chemistry and Center for Chemical Methodology and Library Development, Boston University, 590 Commonwealth Avenue, Boston, Massachusetts 02215, USA
    Org Lett 6:525-8. 2004
    ....
  22. ncbi request reprint Azetidinic amino acids: stereocontrolled synthesis and pharmacological characterization as ligands for glutamate receptors and transporters
    Hans Brauner-Osborne
    Department of Medicinal Chemistry, Danish University of Pharmaceutical Sciences, Universitetsparken 2, DK 2100, Copenhagen, Denmark
    Org Biomol Chem 3:3926-36. 2005
    ..At EAAT1-3, compound 35 was inactive, whereas azetidines 36 and 40 were both identified as inhibitors and showed selectivity for the EAAT2 subtype...