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Dominique Cahard Directeur de Recherche CNRS UMR 6014 CNRS C.O.B.R.A. Université de Rouen, 76821 Mont-Saint-Aignan Phone : 02 35 52 24 66 or (24 23) E-mail : [email protected] PERSONAL
Male, born 20th March 1968 (France). Nationality : French EXPERIENCE
10/2007 – present : Directeur de Recherche CNRS 10/1996 – 9/2007 : Chargé de Recherche CNRS 2/1996 – 4/1996 : Postdoctoral Fellow with Pr Tadashi Nakata (RIKEN, Tokyo, Japan) « Total synthesis of Mycalamide A » 2/1994 – 5/1995 : Postdoctoral Fellow with Pr. Chris McGuigan (School of Pharmacy, Cardiff, Wales) « Design, synthesis, and biological evaluation of anti-HIV nucleotide progrugs » EDUCATION
2001 : Habilitation à diriger des Recherches 1994 : Ph.D., University of Rouen, France (Under the supervision of Prs Jean Marie Poirier & Pierre Duhamel) « Novel route to enolate from silyl enol ethers and enol acetates. Reaction with hard and soft electrophiles » RESEARCH FIELDS
Asymmetric synthesis – Fluorine Chemistry – Catalysis – Medicinal chemistry TEACHING EXPERIENCE
Organofluorine Chemistry (Master courses) – Chemical literature search (Master & PhD courses) COLLABORATIONS
Pr Jun-An Ma (Tianjin University, China) – Pr Norio Shibata (Nagoya University, Japan) – Dr Barbara Mohar (Slovenia) – Pr Jean-Luc Renaud (Caen University, France) – Pr Herbert Mayr (Universitaet Muenchen, Germany) – Dr Kosuke Kawada (Tosoh F-Tech, Japan)
I am author of 93 research articles, 4 patents, 10 book chapters, 52 invited lectures
Web of Science®
Results found: 92 Sum of the times cited : 4472 Average citations per item : 50.1 h-index : 33
Publications 2015 – 2008 “Regio- and Stereocontrolled Nucleophilic Trifluoromethylthiolation of Morita-Baylis-Hillman Carbonates.” X. Dai, D. Cahard* Synlett, 40–44, 2015
“Enantioselective Synthesis of α-CF3 Arylmethylamines by Ruthenium-Catalyzed Transfer Hydrogenation Reaction.” X. Dai, D. Cahard* Adv. Synth. Catal., 356, 1317-1328, 2014
“Recent Progress in Asymmetric Fluorination and Trifluoromethylation Reactions.” V. Bizet, T. Besset, J.A. Ma, D. Cahard* Curr. Top. Med. Chem., 14, 901-940, 2014
“Regio- and Diastereoselective Cu-Mediated Trifluoromethylation of Functionalized Alkenes.” T. Besset,* D. Cahard*, X. Pannecoucke J. Org. Chem. 79, 413–418, 2014
“Rescue of Fragile X Syndrome Phenotypes in Fmr1 KO Mice by a BKCa Channel Opener Molecule” B. Hebert, S. Pietropaolo, S. Même, B. Laudier, A. Laugeray, N. Doisne, A. Quartier, S. Lefeuvre, L. Got, D. Cahard, F. Laumonnier, W. Crusio, J. Pichon, A. Menuet, O. Perche, S. Briault* Orphanet Journal of Rare Diseases, 9:124, 2014
“The influence of fluorine in asymmetric catalysis.” D. Cahard*, V. Bizet Chem. Soc. Rev., 43, 135–147, 2014
“Fluorine as Control Element in Asymmetric Synthesis” D. Cahard*, V. Bizet Chimia, 68, 378–381, 2014
“Chiral NFSI Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination.” C-L. Zhu, M. Maeno, F-G Zhang, T. Shigehiro, T. Kagawa, K. Kawada, N. Shibata,* J-A. Ma,* D. Cahard* Eur. J. Org. Chem., 6501–6505, 2013
“Iron (II) complexes are suitable catalysts for isomerization of trifluoromethylated allylic alcohols.” D. Cahard,* V. Bizet, X. Dai, S. Gaillard, J. L. Renaud* J. Fluorine Chem., 155, 78–82, 2013
“Fluorinated pseudopeptide analogues of the neuropeptide 26RFa : synthesis, biological and structural studies.” C. Pierry, S. Couve-Bonnaire,* L. Guilhaudis, C. Neveu, A. Marotte,
B. Lefranc, D. Cahard, I. Ségalas-Milazzo, J. Leprince, X. Pannecoucke* ChemBioChem., 14, 1620-1633, 2013
“Ruthenium-Catalyzed One-pot Tandem Isomerization–Transfer Hydrogenation Reactions of γ-CF3 Allylic Alcohols and β-CF3 Enones.” V. Bizet, X. Pannecoucke, J. L. Renaud,* D. Cahard* Adv. Synth. Catal., 355, 1394-1402, 2013
“P-Spiro Phosphonium Salts Catalyzed Asymmetric Fluorination of 3-Substituted Benzofuran-2(3H)-ones.” C-L. Zhu, X-Y. Fu, A-J. Wei, J. Nie, D. Cahard,* J-A. Ma* J. Fluorine Chem., 150, 60-66, 2013
“Isomérisation rédox : une réaction économe en atome à fort potentiel d’innovation.” V. Bizet, D. Cahard, S. Gaillard, J. L. Renaud Les Techniques de l’Ingénieur, in159 (8-2013), 2013
“Synthesis of β-CF3 Ketones from Trifluoromethylated Allylic Alcohols by Ruthenium Catalyzed Redox Isomerization.” V. Bizet, X. Pannecoucke, J. L. Renaud, D. Cahard* J. Fluorine Chem., 152, 56-61, 2013
“Ruthenium Catalyzed Redox Isomerization of Trifluoromethylated Allylic Alcohols: Mechanistic Evidence for an Enantiospecific Pathway” V. Bizet, X. Pannecoucke, J. L. Renaud,* D. Cahard* Angew. Chem. Int. Ed., 51, 6467-6470, 2012
“Tamed Arene and Heteroarene Trifluoromethylation” T. Besset, C. Schneider, D. Cahard* Angew. Chem. Int. Ed., 51, 5048-5050, 2012
“Asymmetric Fluorination Methods and their Application for the Stereoselective Synthesis of Fluorinated Drugs” V. Bizet, D. Cahard* Stereoselective Synthesis of Drugs and Natural Products (chapter 37). Publisher: Wiley-Blackwell. In press 2012
“Synthesis of α-CF3-substituted carbonyl compounds with relative and absolute stereocontrol using electrophilic CF3-transfer reagents” V. Matoušek, A. Togni, V. Bizet, D. Cahard Org. Lett., 13, 5762-5765, 2011 and Synfact, 8(1), 81, 2012
“Construction of Trifluoromethyl-Bearing Quaternary Carbon Centers by Intramolecular Decarboxylative Allylation of α -Trifluoromethyl β-Keto Esters” N. Shibata, S. Suzuki, T. Furukawa, H. Kawai, E. Tokunaga, Y. Zhe, D. Cahard Adv. Synth. Catal., 353, 2037-2041, 2011
“Enantioselective Base-Free Electrophilic Amination of Benzofuran-2(3H)-ones: Catalysis by Binol-Derived P-Spiro Quaternary Phosphonium Salts” C-L. Zhu, F-G. Zhang, W. Meng, J. Nie, D. Cahard, J-A Ma* Angew. Chem. Int. Ed., 50, 5869-5872, 2011
“Diastereoselective Synthesis of trans-Trifluoromethyl-β-Lactams and α-Alkyl-β-Trifluoromethyl-β-Amino Esters” V. Petrik, G-V. Röeschenthaler, D. Cahard Tetrahedron, 67, 3254-3259, 2011
“Asymmetric Construction of Stereogenic Carbon Centers Featuring a Trifluoromethyl Group from Prochiral Trifluoromethylated Substrates” J. Nie, H-C. Guo, D. Cahard, J-A Ma Chem. Rev., 111, 455-529, 2011
“Metal Mediated Reversal of Stereochemistry in Diastereoselective Addition of Organometallic Reagents to N-(tert-butanesulfinyl)-α-fluoroenimines” C. Pierry, D. Cahard, S. Couve-Bonnaire, X. Pannecoucke Org. Biomol. Chem., 9, 2378-2386, 2011
“Shelf-stable Electrophilic Trifluoromethylating Reagents: A Brief Historical Perspective.” N. Shibata, A. Matsnev, D. Cahard Beilstein J. Org. Chem., 6, No. 65, 2010
“Fluorine & Chirality: How to Create a Nonracemic Stereogenic Carbon-Fluorine Centre?” D. Cahard, X. Xu, S. Couve-Bonnaire, X. Pannecoucke Chem. Soc. Rev., 39, 558-568, 2010
“Enantioselective electrophilic trifluoromethylation of β-keto esters with Umemoto reagents induced by chiral nonracemic guanidines” S. Noritake, N. Shibata, Y. Nomura, Y. Huang, A. Matsnev, S. Nakamura, T. Toru, D. Cahard Org. Biomol. Chem., 7, 3599-3604, 2009
“Radical Conjugated Addition (RCA): Addition of Dialkyl Difluoromethylenephosphonate Radical onto Unsaturated Ketones” A. Sène, S. Diab, A. Hienzsch, D. Cahard, T. Lequeux Synlett, 981-985, 2009
“Diastereocontrolled addition of organometallic reagents to S-chiral N-(tert-butanesulfinyl)-α-fluoroenimines” C. Pierry, L. Zoute, P. Jubault, T. Lequeux, D. Cahard, S. Couve-Bonnaire, X. Pannecoucke Tetrahedron Lett., 50, 264-266, 2009
“Asymmetric Fluorination, Trifluoro-methylation and Perfluoroalkylation Reactions” J-A. Ma, D. Cahard* Chem. Rev., 108 (9), PR1–PR43, 2008
Invited lectures 2015 – 2010 “Regio- and stereoselective trifluoromethylthiolation reactions” 22nd Winter Fluorine Conference, St. Pete Beach, Florida (Etats-Unis), 11-16/01/2015
“Stereoselective Hydride Transfer Reactions for the Construction of Chiral Trifluoromethylated Molecules.” 37th Fluorine Conference of Japan, Osaka (Japon), 30-31/10/2014
“Influence of Fluorine in Asymmetric Synthesis.” 248th ACS National Meeting, San Francisco, California (USA), 10-14/8/2014
“Enantioselective Metal-Catalyzed Hydride Transfer Reactions for the Construction of CF3 Stereogenic Carbon Centres” The Pregl Colloquium, National Institute of Chemistry Slovenia, Ljubljana (Slovénie), 5/6/2014
“Asymmetric Hydride Transfer Reactions for the Construction of Chiral CF3 compounds.” 2nd International Workshop on Organofluorine Chemistry, Nanjing (China), 12-14/9/2013
“Enantioselective Metal-Catalyzed Hydride Transfer Reactions for the Construction of CF3 Stereogenic Carbon Centres.” Fluorine Graduate School, Freie Universität & Humboldt Universität Berlin (Germany), 25-26/6/2013
“Metal-Catalyzed Hydride Transfer Reactions: Enantioselective Construction of CF3–Substituted Carbon Centres.” 4th Tokyo International Workshop on Fluorine Chemistry, Tokyo (Japan), 13-14/4/2013
“Construction of CF3–Stereogenic Carbon Centers by Ruthenium-Catalyzed Isomerization and Transfer hydrogenation.” 245th ACS National Meeting, New Orleans, Louisiana (USA), 7-11/4/2013
“Chiral Brønsted Acid-Catalyzed Diastereo- and Enantioselective Synthesis of CF3-Substituted Aziridines” 20th International Symposium on Fluorine Chemistry, Kyoto (Japan), 22-27/7/2012
“Redox Isomerization of Fluorinated Allylic Alcohols” Valencia Fluorine Days Symposium on Fluorine Chemistry, Valence (Spain), 20-24/5/2012
“Stereoselective Construction of CF3-Bearing Stereogenic Carbon Centres” International Workshop on Organofluorine Chemistry, Nankai (China), 28-30/10/2011
“Transformation of CF3-bearing substrates versus direct trifluoromethylation” 8th French Colloquium on Fluorine Chemistry, Strasbourg (France), 20-24/3/2011
“Stereoselective Synthesis of Fluorinated Compounds” 11th Annual Meeting on Fluorine Chemistry, Shanghai (China), 13-16/10/2010
