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Publications de l’équipe

AccueilDépartements de rechercheDépartement de Synthèse Organique et Méthodes...Chimie du Phosphore et CatalysePublications de l’équipe

2024

  • [DOI] Soualmia, F.; Cherrier, M.; Chauviré, T.; Mauger, M.; Tatham, P.; Guillot, A.; Guinchard, X.; Martin, L.; Amara, P.; Mouesca, J.-M.; Daghmoum, M.; Benjdia, A.; Gambarelli, S.; Berteau, O.; Nicolet, Y.. Radical S-adenosyl-l-methionine Enzyme Pylb: A C-centered Radical to Convert l-lysine into (3r)-3-methyl-d-ornithine. Journal of the American Chemical Society 2024. doi:10.1021/jacs.3c03747

2023

  • [DOI] Buttard, F.; Guinchard, X.. Spiroindoles as Intermediates/products in Transition Metal-catalyzed Dearomatization of Indoles. ACS Catalysis 2023, 13 (14), 9442–9475. doi:10.1021/acscatal.3c01417
  • [DOI] Losa, R.; Lorton, C.; Retailleau, P.; Bignon, J.; Voituriez, A.. Fluorinated 2-azetines: Synthesis, Applications, Biological Tests, and Development of a Catalytic Process. Organic Letters 2023, 25 (27), 5140–5144. doi:10.1021/acs.orglett.3c01888
  • [DOI] Jia, T.; Diane, O.; Ghosh, D.; Skander, M.; Fontaine, G.; Retailleau, P.; Poupon, J.; Bignon, J.; Siasia, Y.; Servajean, V.; Hue, N.; Betzer, J.-F.; Marinetti, A.; Bombard, S.. Anti-cancer and Radio-sensitizing Properties of New Bimetallic (n-heterocyclic Carbene)-amine-pt(ii) Complexes. Journal of Medicinal Chemistry 2023, 66 (10), 6836–6848. doi:10.1021/acs.jmedchem.3c00267
  • [DOI] Zhou, W.; Voituriez, A.. Total Synthesis of (-)-hm-30.167emand (-)-HM-4 Using an Asymmetric Gold-catalyzed [3,3]-sigmatropic Rearrangement of Sulfonium. European Journal of Organic Chemistry 2023, 26 (17). doi:10.1002/ejoc.202300126
  • [DOI] Betzer, J.-F.; Arcile, G.; MASSARD, T.; Elslande, E.; Ouazzani, J.. Biomimetic-inspired Synthesis of Sporochartines Through Diels-alder Reaction Between Enantiopure (-)-sporothriolide and (+)-trienylfuranol A. Organic Chemistry Frontiers 2023. doi:10.1039/d3qo00971h
  • [DOI] Yu, Y.; Sabat, N.; Daghmoum, M.; Zhang, Z.; Retailleau, P.; Frison, G.; Marinetti, A.; Guinchard, X.. Enantioselective Au(i)-catalyzed Tandem Reactions Between 2-alkynyl Enones and Naphthols by the Tethered Counterion-directed Catalysis Strategy. Organic Chemistry Frontiers 2023, 10 (12), 2936–2942. doi:10.1039/d3qo00415e

2022

  • [DOI] Gaignard-Gaillard, Q.; Han, X.; Alix, A.; Bour, C.; Guillot, R.; Gandon, V.; Voituriez, A.. Atroposelective Synthesis of Tetrahydropyrrolo[3,2-c]azepine Derivatives Through Gold(i)-catalyzed Hydroarylation. Advanced Synthesis & Catalysis 2022, 364 (24), 4415–4420. doi:10.1002/adsc.202200828
  • [DOI] Sabat, N.; Zhou, W.; Gandon, V.; Guinchard, X.; Vincent, G.. Unbiased C3-electrophilic Indoles: Triflic Acid Mediated C3-regioselective Hydroarylation of N-H Indoles. Angew. Chem. Int. Ed. 2022, 134 (30). doi:10.1002/ange.202204400
  • [DOI] Sabat, N.; Zhou, W.; Gandon, V.; Guinchard, X.; Vincent, G.. Unbiased C3‐electrophilic Indoles: Triflic Acid Mediated C3‐regioselective Hydroarylation of N−H Indoles**. Angewandte Chemie International Edition 2022, 61 (30). doi:10.1002/anie.202204400
  • [DOI] Soualmia, F.; Guillot, A.; Sabat, N.; Brewee, C.; Kubiak, X.; Haumann, M.; Guinchard, X.; Benjdia, A.; Berteau, O.. Exploring the Biosynthetic Capacity of TsrM , a B12-dependent Radical SAM Enzyme Catalyzing Non-radical Reactions. Chem. Eur. J. 2022, e202200627. doi:10.1002/chem.202200627
  • [DOI] Zhang, Z.; Sabat, N.; Frison, G.; Marinetti, A.; Guinchard, X.. Enantioselective Au(i)-catalyzed Multicomponent Annulations via Tethered Counterion-directed Catalysis. ACS Catalysis 2022, 12 (7), 4046–4053. doi:10.1021/acscatal.2c00120
  • [DOI] Arcile, G.; Ouazzani, J.; Betzer, J.-F.. Efficient Piancatelli Rearrangement on a Large Scale Using the Zippertex Technology Under Subcritical Water Conditions. Reaction Chemistry aEngineering 2022, 7 (7), 1640–1649. doi:10.1039/d2re00098a
  • [DOI] Han, X.; Gaignard-Gaillard, Q.; Retailleau, P.; Gandon, V.; Voituriez, A.. Synthesis of Chiral Polycyclic N-heterocycles via Gold(i)-catalyzed 1,6-enyne Cyclization/intramolecular Nucleophilic Addition. Chemical Communications 2022, 58 (18), 3043–3046. doi:10.1039/d1cc06388j
  • [DOI] Ferry, A.; Guinchard, X.. Bicyclic 5-5 Systems with One Bridgehead (ring Junction) Nitrogen Atom: Two Extra Heteroatoms 1:1. Comprehensive Heterocyclic Chemistry IV 2022, 95–144. doi:10.1016/b978-0-12-409547-2.14934-0

2021

  • [DOI] Zhou, W.; Voituriez, A.. Gold(i)-catalyzed Synthesis of Highly Substituted 1,4-dicarbonyl Derivatives via Sulfonium [3,3]-sigmatropic Rearrangement. Org. Lett. 2021, 23, 247–252. doi:10.1021/acs.orglett.0c04023
  • [DOI] Zhou, W.; Voituriez, A.. Synthesis of Cyclopentenones with C4-quaternary Stereocenters via Stereospecific [3,3]-sigmatropic Rearrangement and Applications in Total Synthesis of Sesquiterpenoids. J. Am. Chem. Soc. 2021, 143, 17348–17353. doi:10.1021/jacs.1c07966
  • [DOI] Lorton, C.; Roblin, A.; Retailleau, P.; Voituriez, A.. Synthesis of Functionalized Cyclobutenes and Spirocycles via Asymmetric P( III )/P(V) Redox Catalysis. Adv. Synth. Catal. 2021, 363, 4805–4810. doi:10.1002/adsc.202100664
  • [DOI] Lorton, C.; Saleh, N.; Voituriez, A.. Phosphine‐catalyzed Synthesis of Chiral N‐heterocycles Through (asymmetric) P(III)/P(V) Redox Cycling. European Journal of Organic Chemistry 2021, 2021 (22), 3340–3344. doi:10.1002/ejoc.202100404
  • [DOI] Arcile, G.; Retailleau, P.; Ouazzani, J.; Betzer, J.-F.. Total Synthesis of the Fungal Metabolite Trienylfuranol A Through Nucleophilic Diastereodivergent Additions to Oxocarbenium Ions. European Journal of Organic Chemistry 2021, 2021 (13), 2050–2054. doi:10.1002/ejoc.202100265
  • [DOI] Milcendeau, P.; Zhang, Z.; Glinsky-Olivier, N.; Elslande, E.; Guinchard, X.. Au(i)-catalyzed Pictet – Spengler Reactions All Around the Indole Ring. J. Org. Chem. 2021, 86, 6406–6422. doi:10.1021/acs.joc.1c00270
  • [DOI] Milcendeau, P.; Gandon, V.; Guinchard, X.. Gold-catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration. Adv. Synth. Catal. 2021, 363, 2893–2902. doi:10.1002/adsc.202100007
  • [DOI] Cacheux, F.; Goff, G.; Ouazzani, J.; Bignon, J.; Retailleau, P.; Marinetti, A.; Voituriez, A.; Betzer, J.-F.. The Piancatelli Rearrangement of Non-symmetrical Furan-2,5-dicarbinols for the Synthesis of Highly Functionalized Cyclopentenones. Org. Chem. Front. 2021, 8, 2. doi:10.1039/d1qo00268f
  • [DOI] Yu, Y.; Zhang, Z.; Voituriez, A.; Rabasso, N.; Frison, G.; Marinetti, A.; Guinchard, X.. Enantioselective Au(i)-catalyzed Dearomatization of 1-naphthols with Allenamides Through Tethered Counterion-directed Catalysis. Chem. Commun. 2021, 57, 10779–10782. doi:10.1039/d1cc04088j
  • [DOI] Goual, N.; Casimiro, L.; Delattre, V.; Retailleau, P.; Maisonneuve, S.; Bogliotti, N.; Métivier, R.; Xie, J.; Marinetti, A.; Voituriez, A.. Triazonine-based Bistable Photoswitches: Synthesis, Characterization and Photochromic Properties. Chemical Communications 2021, 57 (78), 10079–10082. doi:10.1039/d1cc02746h
  • [DOI] Cazorla, C.; Casimiro, L.; Arif, T.; Deo, C.; Goual, N.; Retailleau, P.; Métivier, R.; Xie, J.; Voituriez, A.; Marinetti, A.; Bogliotti, N.. Synthesis and Properties of Photoswitchable Diphosphines and Gold(i) Complexes Derived from Azobenzenes. Dalton Transactions 2021, 50 (21), 7284–7292. doi:10.1039/d1dt01080h

2020

  • [DOI] Medici, F.; Goual, N.; Delattre, V.; Voituriez, A.; Marinetti, A.. Photoswitchable Phosphines in Catalysis. ChemCatChem 2020, 12, 5573–5589. doi:10.1002/cctc.202000620
  • [DOI] Sabat, N.; Soualmia, F.; Retailleau, P.; Benjdia, A.; Berteau, O.; Guinchard, X.. Correction to Gold-catalyzed Spirocyclization Reactions of N-propargyl Tryptamines and Tryptophans in Aqueous Media. Org. Lett. 2020, 22, 5714–5714. doi:10.1021/acs.orglett.0c02206
  • [DOI] Magné, V.; Sanogo, Y.; Demmer, C.; Retailleau, P.; Marinetti, A.; Guinchard, X.; Voituriez, A.. Chiral Phosphathiahelicenes: Improved Synthetic Approach and Uses in Enantioselective Gold(i)-catalyzed [2 + 2] Cycloadditions of N-homoallenyl Tryptamines. ACS Catalysis 2020, 10, 8141–8148. doi:10.1021/acscatal.0c01819
  • [DOI] Sabat, N.; Soualmia, F.; Retailleau, P.; Benjdia, A.; Berteau, O.; Guinchard, X.. Gold-catalyzed Spirocyclization Reactions of N-propargyl Tryptamines and Tryptophans in Aqueous Media. Org. Lett. 2020, 22, 4344–4349. doi:10.1021/acs.orglett.0c01370
  • [DOI] Zhang, Z.; Smal, V.; Retailleau, P.; Voituriez, A.; Frison, G.; Marinetti, A.; Guinchard, X.. Tethered Counterion-directed Catalysis: Merging the Chiral Ion-pairing and Bifunctional Ligand Strategies in Enantioselective Gold(i) Catalysis. J. Am. Chem. Soc. 2020, 142, 3797–3805. doi:10.1021/jacs.9b11154
  • [DOI] Han, X.; Retailleau, P.; Gandon, V.; Voituriez, A.. Enantioselective Gold(i)-catalyzed Cyclization/intermolecular Nucleophilic Additions of 1,5-enyne Derivatives. Chem. Commun. 2020, 56, 9457–9460. doi:10.1039/d0cc00914h
  • [DOI] Milcendeau, P.; Sabat, N.; Ferry, A.; Guinchard, X.. Gold-catalyzed Enantioselective Functionalization of Indoles. Org. Biomol. Chem. 2020, 18, 6006–6017. doi:10.1039/d0ob01245a

2019

  • [DOI] Febvay, J.; Demmer, C.; Retailleau, P.; Crassous, J.; Abella, L.; Autschbach, J.; Voituriez, A.; Marinetti, A.. Phosphahelicenes with (thio)phosphinic Acid and Ester Functions by the Oxidative Photocyclisation Approach. Chem. Eur. J. 2019, 25, 15609–15614. doi:10.1002/chem.201903750
  • [DOI] Febvay, J.; Sanogo, Y.; Retailleau, P.; Gogoi, M.; Sahoo, A.; Marinetti, A.; Voituriez, A.. Enantioselective Gold(i)-catalyzed Hydrative Cyclizations of N-propargyl-ynamides into 3,6-dihydropyridinones. Organic Letters 2019, 21, 9281–9285. doi:10.1021/acs.orglett.9b02644
  • [DOI] Glinsky-Olivier, N.; Yang, S.; Retailleau, P.; Gandon, V.; Guinchard, X.. Enantioselective Gold-catalyzed Pictet – Spengler Reaction. Org. Lett. 2019, 21, 9446–9451. doi:10.1021/acs.orglett.9b03656
  • [DOI] Lorton, C.; Voituriez, A.. Synthesis and Applications of 9H -pyrrolo[1,2-a ]indole and 9H -pyrrolo[1,2-a ]indol-9-one Derivatives. Eur. J. Org. Chem. 2019, 2019, 5133–5150. doi:10.1002/ejoc.201900626
  • [DOI] Mallick, R.; Dutta, S.; Vanjari, R.; Voituriez, A.; Sahoo, A.. Thioarylative Radical Cyclization of Yne-dienone. J. Org. Chem. 2019, 84, 10509–10517. doi:10.1021/acs.joc.9b01445
  • [DOI] Lorton, C.; Castanheiro, T.; Voituriez, A.. Catalytic and Asymmetric Process via PIII / PV ═O Redox Cycling: Access to (trifluoromethyl)cyclobutenes via a Michael Addition/wittig Olefination Reaction. J. Am. Chem. Soc. 2019, 141, 10142–10147. doi:10.1021/jacs.9b02539
  • [DOI] Sanogo, Y.; Aillard, P.; Retailleau, P.; Voituriez, A.; Marinetti, A.. Synthesis and X-ray Diffraction Study of a Chiral Bis-phosphahelicene Palladium ( II ) Complex. Chirality 2019, 31, 561–567. doi:10.1002/chir.23100
  • [DOI] Yavari, K.; Delaunay, W.; Rycke, N. D.; Reynaldo, T.; Aillard, P.; Srebro-Hooper, M.; Chang, V.; Muller, G.; Tondelier, D.; Geffroy, B.; Voituriez, A.; Marinetti, A.; Hissler, M.; Crassous, J.. Phosphahelicenes: From Chiroptical and Photophysical Properties to OLED Applications. Chem. Eur. J. 2019, 25, 5303–5310. doi:10.1002/chem.201806140

2018

  • [DOI] Marinetti, A.. The Institut De Chimie Des Substances Naturelles ( ICSN ): Past and Present. European Journal of Organic Chemistry 2018, 2018 (42), 5774–5776. doi:10.1002/ejoc.201801558
  • [DOI] Aillard, P.; Gicquel, M.; Yavari, K.; Retailleau, P.; Voituriez, A.; Marinetti, A.. Tuning the Structure of Phosphahelicenes for Targeted Applications in Enantioselective Phosphine Organocatalysis. Eur. J. Org. Chem. 2018, 2018, 5853–5860. doi:10.1002/ejoc.201800438
  • [DOI] Arif, T.; Cazorla, C.; Bogliotti, N.; Saleh, N.; Blanchard, F.; Gandon, V.; Metivier, R.; Xie, J.; Voituriez, A.; Marinetti, A.. Bimetallic Gold(i) Complexes of Photoswitchable Phosphines: Synthesis and Uses in Cooperative Catalysis. Catalysis Science & Technology 2018, 8 (3), 710–715. doi:10.1039/C7CY01614J
  • [DOI] Force, G.; Ki, Y.; Isaac, K.; Retailleau, P.; Marinetti, A.; Betzer, J.. Paracyclophane-based Silver Phosphates as Catalysts for Enantioselective Cycloisomerization/addition Reactions: Synthesis of Bicyclic Furans. Advanced Synthesis & Catalysis 2018, 360 (17), 3356–3366. doi:10.1002/adsc.201800587
  • [DOI] Gicquel, M.; Gomez, C.; Alvarez, M.; Pamlard, O.; Guerineau, V.; Jacquet, E.; Bignon, J.; Voituriez, A.; Marinetti, A.. Inhibition of P53-murine Double Minute 2 (MDM2) Interactions with 3,3'-spirocyclopentene Oxindole Derivatives. Journal of medicinal chemistry 2018, 61 (20), 9386–9392. doi:10.1021/acs.jmedchem.8b01137
  • [DOI] Glinsky-Olivier, N.; Retailleau, P.; Guinchard, X.. Gold-catalyzed Synthesis of Spirofused Indoloquinuclidines. Eur. J. Org. Chem. 2018, 2018, 5823–5829. doi:10.1002/ejoc.201800357
  • [DOI] Gobe, V.; Dousset, M.; Retailleau, P.; Gandon, V.; Guinchard, X.. Dissecting the Gold(i)-catalyzed Carboaminations of N-allyl Tetrahydro-beta-carbolines to Allenes. J. Org. Chem. 2018, 83, 898–912. doi:10.1021/acs.joc.7b02900
  • [DOI] Gobé, V.; Gandon, V.; Guinchard, X.. Reactions Involving Tryptamines and Δ‐allenyl Aldehydes: Competition Between Pictet‐spengler Reaction and Cyclization to 1‐aminotetralins. Adv. Synth. Catal. 2018, 360, 1280–1288. doi:10.1002/adsc.201701487
  • [DOI] Lorton, C.; Voituriez, A.. Phosphine-promoted Synthesis of 9h-pyrrolo 1,2-a Indole Derivatives via an Gamma-umpolung Addition/intramolecular Wittig Reaction. Journal of Organic Chemistry 2018, 83 (10), 5801–5806. doi:10.1021/acs.joc.8b00457
  • [DOI] Magné, V.; Retailleau, P.; Marinetti, A.; Voituriez, A.; Guinchard, X.. Gold-catalyzed Synthesis of 2-sulfenylspiroindolenines via Spirocyclizations. Molbank 2018, M985. doi:10.3390/m985
  • [DOI] Neel, M.; Retailleau, P.; Voituriez, A.; Marinetti, A.. Diastereoselective Synthesis of Planar Chiral Phosphoramidites with a Ferrocenophane Scaffold. Organometallics 2018, 37 (5), 797–801. doi:10.1021/acs.organomet.7b00700
  • [DOI] Pastor, J.; Rezabal, E.; Voituriez, A.; Betzer, J.-F.; Marinetti, A.; Frison, G.. Revised Theoretical Model on Enantiocontrol in Phosphoric Acid Catalyzed H-transfer Hydrogenation of Quinoline. The Journal of Organic Chemistry 2018, 83 (5), 2779–2787. doi:10.1021/acs.joc.7b03248
  • [DOI] Han, X.; Saleh, N.; Retailleau, P.; Voituriez, A.. Phosphine-catalyzed Reaction Between 2-aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction. Organic Letters 2018, 20 (15), 4584–4588. doi:10.1021/acs.orglett.8b01870
Chimie du Phosphore et Catalyse Accueil
Etudiants
CV X. Guinchard
CV A. Voituriez
CV J. F. Betzer
CV A. Marinetti

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