Papers from the group

2020

Au(I)-catalyzed Pictet-Spengler Reactions: a journey around the indole ring Milcendeau, P.; Zhang, Z.; Glinsky-Olivier, N.; van Elslande, E.; Guinchard, X.*, ChemRxiv. 2020. Freely available

Gold-Catalyzed Enantioselective Functionalizations of Indoles Milcendeau, P.; Sabat, N.; Ferry, A.*; Guinchard, X.*, Org. Biomol. Chem. 2020, 18, 6006. DOI 10.1039/D0OB01245A

Enantioselective gold(I)-catalyzed cyclization/intermolecular nucleophilic additions of 1,5-enyne derivatives Han, X.; Retailleau, P.; Gandon, V.;* Voituriez, A.* Chem. Commun. 2020, 56, 9457-9460. DOI: 10.1039/D0CC00914H

Photoswitchable phosphines in catalysis Medici, F.; Goual, N.; Delattre V.; Voituriez, A.;* Marinetti, A.* ChemCatChem 2020. DOI : 10.1002/cctc.202000620

Gold-Catalyzed Spirocyclization Reactions of N-Propargyl Tryptamines and Tryptophans in Aqueous Media. Sabat, N.; Soulamia, F.; Retailleau, P.; Benjdia, A.; Berteau, O.; Guinchard, X.* Org. Lett. 2020, 22, 4344. DOI 10.1021/acs.orglett.0c01370

Chiral Phosphathiahelicenes: Improved Synthetic Approach and Uses in Enantioselective Gold(I)-Catalyzed [2+2] Cycloadditions of N-Homoallenyl Tryptamines. Magné, V. ; Sanogo, Y; Demmer, C. S.; Retailleau, P. ; Marinetti, A. ; Guinchard, X.*; Voituriez, A. * , ACS Catal., 2020, 10, 8141.DOI 10.1021/acscatal.0c01819

Gold-Catalyzed Spirocyclization Reactions of N-Propargyl Tryptamines and Tryptophans in Aqueous Media. Sabat, N.; Soulamia, F.; Retailleau, P.; Benjdia, A.; Berteau, O.; Guinchard, X.* Org. Lett. 2020, 22, 4344. Also accessible freely : ChemRxiv. 2020, DOI 10.26434/chemrxiv.12136782.v1

Tethered Counterion-Directed Catalysis: Merging the Chiral Ion-pairing and Bifunctional Ligand Strategies in Enantioselective Gold(I) Catalysis. Zhang, Z..; Smal, V.; Retailleau, P.; Voituriez, A.; Frison, G.; Marinetti, A.* ; Guinchard, X.* J. Am. Chem. Soc. 2020, DOI 10.1021/jacs.9b11154

2019

Enantioselective Au(I)-Catalyzed Pictet-Spengler Reactions. Glinsky-Olivier, N.; Shengwen, Y.; Retailleau, P.; Gandon, V.* ; Guinchard, X.* Org. Lett. 2019, 21, 9446. DOI : 10.1021/acs.orglett.9b03656

Phosphahelicenes: from chiroptical and photophysical properties to OLED applications. Yavari, K.; Delaunay, W.; De Rycke, N.; Reynaldo, T.; Aillard, P.; Srebro-Hooper,* M.; Chang, V. Y.; Muller, G.; Tondelier, D.; Geffroy, B.; Voituriez,* A.; Marinetti,*A.; Hissler,* M.; Crassous,* J. Chem. Eur. J. 2019, 20, 5303-5310. DOI: 10.1002/chem.201806140

Catalytic and Asymmetric Process via P^III/P^V=O Redox Cycling: Access to (Trifluoromethyl)cyclobutenes via a Michael Addition/Wittig Olefination Reaction. Lorton, C.; Castanheiro, T.; Voituriez,* A. J. Am. Chem. Soc. 2019, 141, 10142-10147. DOI: 10.1021/jacs.9b02539

Synthesis and X-ray diffraction study of a chiral bis-phosphahelicene palladium (II) complex. Sanogo, Y.; Aillard, P.; Retailleau, P.; Voituriez,* A.; Marinetti,* A. Chirality 2019, 8, 561-567. DOI: 10.1002/chir.23100

Synthesis and Applications of 9H-Pyrrolo[1,2-a]indole and 9H-Pyrrolo[1,2-a]indol-9-one Derivatives. Lorton C.; Voituriez,* A. Eur. J. Org. Chem. 2019, 5133-5150. DOI: 10.1002/ejoc.201900626

Thioarylative Radical Cyclization of Yne-Dienone. Mallick, R.K.; Dutta, S.; Vanjari, R.; Voituriez, A.; Sahoo, A.K. J. Org. Chem. 2019, 84, 10509-10517. DOI: 10.1021/acs.joc.9b01445

Phosphahelicenes with (thio)phosphinic acid and ester functions via the oxidative photocyclisation approach. Febvay, J.; Demmer, C.; Retailleau, P.; Crassous, J.; Abella, L.; Autschbach, J.;* Voituriez,* A.; Marinetti, A.* Chem. Eur. J. 2019, 25, 15609-15614. DOI: 10.1002/chem.201903750.

Enantioselective Gold(I)-Catalyzed Hydrative Cyclizations of N-Propargyl Ynamides into 3,6-Dihydropyridinones. Febvay, J.; Sanogo, Y.; Retailleau, P.; Gogoi, M.P.; Sahoo, A.K.; Marinetti, A.;* Voituriez, A.* 2019, 21, 9281-9285. DOI: 10.1021/acs.orglett.9b02644

2018

Inhibition of p53-Murine Double Minute 2 (MDM2) Interactions with 3,3′-Spirocyclopentene Oxindole Derivatives Gicquel, M.; Gomez, C.; Garcia Alvarez, M. C.; Pamlard, O.; Guérineau, V.; Jacquet, E.; Bignon, J.;* Voituriez, A.;* Marinetti, A.* J. Med. Chem. 2018, 61, 9386-9392. DOI : 1 0.1021/acs.jmedchem.8b01137

Tuning the Structure of Phosphahelicenes for Targeted Applications in Enantioselective Phosphine Organocatalysis Aillard, P.; Gicquel, M.; Yavari, K.; Retailleau, P.; Voituriez, A.;* Marinetti, A.* Eur. J. Org. Chem. 2018, 5853-5860. DOI : 10.1002/ejoc.201800438

Diastereoselective Synthesis of Planar Chiral Phosphoramidites with a Ferrocenophane Scaffold Neel, M.; Retailleau, P.; Voituriez, A.;* Marinetti, A.* Organometallics 2018, 37, 797-801. DOI : 10.1021/acs.organomet.7b00700

Paracyclophane-based Silver Phosphates as Catalysts for Enantioselective Cycloisomerization/Addition Reactions : Synthesis of Bicyclic Furans. Pastor, J. ; Rezabal, E. ; Voituriez, A. ; Betzer,* J.-F. ; Marinetti, A. ; Frison,* G. J. Org. Chem. 2018, 83, 2779. DOI : 10.1021/acs.joc.7b03248

Paracyclophane-based Silver Phosphates as Catalysts for Enantioselective Cycloisomerization/Addition Reactions : Synthesis of Bicyclic Furans. Force, G. ; Lock Toy Ki, Y. ; Isaac, K. ; Retailleau, P. ; Marinetti,* A. ; Betzer,* J.-F. Adv. Synth. Catal. 2018, 360, 1280. DOI : 10.1002/adsc.201800587

Reactions Involving Tryptamines and δ-Allenyl Aldehydes : Competition between Pictet-Spengler Reaction and Cyclization to 1-Aminotetralins. Gobé, V. ; Gandon, V.* ; Guinchard, X.* Adv. Synth. Catal. 2018, 360, 1280. DOI : 10.1002/adsc.201701487

Phosphine-Catalyzed Reaction Between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates : Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction. Han, X. ; Saleh, N. ; Retailleau, P. ; Voituriez, A.* Org. Lett. 2018, DOI : 10.1021/acs.orglett.8b01870.

Phosphine-Promoted Synthesis of 9H-Pyrrolo[1,2-a]indole Derivatives via an γ-Umpolung Addition/Intramolecular Wittig Reaction . Lorton, C. ; Voituriez, A.* J. Org. Chem. 2018, 83, 5801.

Bimetallic gold(I) complexes of photoswitchable phosphines : synthesis and uses in cooperative catalysis . Arif, T. ; Cazorla, C. ; Bogliotti, N. ; Saleh, N. ; Blanchard, F. ; Gandon, V. ; Métivier, R. ; Xie, J. ; Voituriez, A. ;* Marinetti A.* Cat. Sci. Catal. 2018, 8, 710.

Gold-Catalyzed Synthesis of Spirofused Indoloquinuclidines. Glinsky-Olivier, N. ; Retailleau, P. ; Guinchard, X.* Eur. J. Org. Chem. 2018, doi:10.1002/ejoc.201800357 DOI : 10.1002/ejoc.201800357

Dissecting the Gold(I)-Catalyzed Carboaminations of N-Allyl Tetrahydro-β-carbolines to Allenes. Gobé, V. ; Dousset, M. ; Retailleau, P. ; Gandon, V. ; Guinchard, X.* J. Org. Chem. 2018, 83, 898. DOI : 10.1021/acs.joc.7b02900

2017

Synthesis of Nitrogen-Containing Heterocycles and Cyclopentenone Derivatives via Phosphine-Catalyzed Michael Addition/Intramolecular Wittig Reaction. Saleh, N. ; Blanchard, F. ; Voituriez, A. Adv. Synth. Catal. 2017, 359, 2304-2315. DOI : 10.1002/adsc.201700313

Photochemical [2+2] Cyclization of Helical Phosphinamides in Solution and in the Solid State. Demmer, C. S. ; Aillard, P. ; Febvay, J. ; Retailleau, P. ; Voituriez, A. ;* Marinetti, A.* ChemPhotoChem 2017, DOI 10.1002/cptc.201700148.DOI : 10.1002/cptc.201700148

Silyl-Substituted Planar Chiral Phosphoric Acids with Ferrocene-bridged Paracyclophane Frameworks : Synthesis, Characterization, and Uses in Enantioselective aza-Friedel-Crafts Reactions. Stemper, J. ; Isaac, K. ; Ghosh, N. ; Lauwick, H. ; Le Duc, G. ; Retailleau, P. ; Voituriez, A. ; Betzer,* J.-F. ; Marinetti,* A. Adv. Synth. Catal. 2017, 359, 519-526. DOI : 10.1002/adsc.201600920

Enantioselective gold(I)-catalyzed rearrangement of cyclopropyl-substituted 1,6-enynes into 2-oxocyclobutyl-cyclopentanes. Wu, Z. ; Lebœuf, D. ; Retailleau, P. ; Gandon, V.* ; Marinetti, A. ; Voituriez, A.* Chem. Commun. 2017, 53, 7026-7029. DOI : 10.1039/c7cc03234j

Synthesis of Spiroindolenines via Regioselective Gold(I)-Catalyzed Cyclizations of N-Propargyl Tryptamines.Magné, V. ; Marinetti, A. ; Gandon, V.* ; Voituriez, A. ; Guinchard, X.* Adv. Synth. Catal. 2017, 359, 4036. DOI : 10.1002/adsc.201700932

Short Enantioselective Total Synthesis of (−)-Rhazinilam Using a Gold(I)-Catalyzed Cyclization.Magné, V. ; Lorton, C. ; Marinetti, A. ; Guinchard, X. ; Voituriez, A.* Org. Lett. 2017, 19, 4794-4797. DOI : 10.1021/acs.orglett.7b02210

2016

The synthesis of substituted phosphathiahelicenes via regioselective bromination of a preformed helical scaffold : a new approach to modular ligands for enantioselective gold-catalysis. Aillard P. ; Dova, D. ; Magné, V. ; Retailleau, P. ; Cauteruccio, S. ; Licandro, E. ; Voituriez, A.* ; Marinetti, A.* Chem. Commun. 2016, 52, 10984-10987. DOI : 10.1039/C6CC04765C

Synthesis of Spiro[piperidine-3,3’-oxindoles] via Gold(I)-Catalyzed Dearomatization of N-Propargyl- and N-Homoallenyl-2-bromotryptamines.Magné, V. ; Blanchard, F. ; Marinetti, A. ; Voituriez, A.* ; Guinchard, X.* Adv. Synth. Catal. 2016, 358, 3355-3361. DOI : 10.1002/adsc.201600398

Planar Chiral Phosphoramidites with a Paracyclophane Scaffold : Synthesis, Gold(I) Complexes, and Enantioselective Cycloisomerization of Dienynes . Wu, Z. ; Isaac, K. ; Retailleau, P. ; Betzer, J.-F.* ; Voituriez, A.* ; Marinetti, A. Chem. Eur. J. 2016, 22, 3278-3281. DOI : 10.1002/chem.201504658

Synergistic effects in ambiphilic phosphino-borane catalysts for the hydroboration of CO2. Tlili, A. ; Voituriez, A.* ; Marinetti, A.* ; Thuéry, P. ; Cantat, T.* Chem. Commun. 2016, 52, 7553-7555. DOI : 10.1039/C6CC02809H

Gold(I)-Catalyzed Carboaminations of Allenes by N-Allyltetrahydro-β-carbolines : An Experimental and Theoretical Study. Gobé, V. ; Dousset, M. ; Retailleau, P. ; Gandon, V.* ; Guinchard, X.* Adv. Synth. Catal. 2016, 358, 3960-3965.DOI : 10.1002/adsc.201601075

Use of Planar Chiral Ferrocenylphosphine-Gold(I) Complexes in the Asymmetric Cycloisomerization of 3-Hydroxylated 1,5-Enynes.. Wu, Z. ; Retailleau, P. ; Gandon, V. ; Voituriez, A.* ; Marinetti, A.* Eur. J. Org. Chem. 2016, 1, 70-75. DOI : 10.1002/ejoc.201501121

Synthesis of 9H-Pyrrolo[1,2-a]indole and 3H-Pyrrolizine Derivatives via a Phosphine-Catalyzed Umpolung Addition/Intramolecular Wittig Reaction. Saleh, N. ; Voituriez, A.* J. Org. Chem. 2016, 81, 4371-4377. DOI : 10.1021/acs.joc.6b00473

From Phosphine-Promoted to Phosphine-Catalyzed Reactions by in situ Phosphine Oxide Reduction. Voituriez, A.* ; Saleh, N. Tetrahedron Lett. 2016, 57, 4443-4451. DOI : http://dx.doi.org/10.1016/j.tetlet.2016.08.036

Linking of Antitumor trans NHC-Pt(II) Complexes to G-Quadruplex DNA Ligand for Telomeric Targeting.Betzer, J.-F. ; Nuter, F. ; Chtchigrovsky, M. ; Hamon, F. ; Kellermann, G. ; Ali, S. ; Calméjane, M.-A. ; Roque, J. ; Poupon, J. ; Cresteil, T. ; Teulade-Fichou, M.-P. ; Marinetti, A.* ; Bombard, S.* Bioconjugate Chem. 2016, 27, 1456–1470. DOI : 10.1021/acs.bioconjchem.6b00079

2015

Synthesis of New Phosphahelicene Scaffolds and Development of Gold(I)-Catalyzed Enantioselective Allen-ene Cyclizations.Aillard P. ; Retailleau, P. ; Voituriez, A.* ; Marinetti, A.* Chem. Eur. J. 2015, 21, 11989-11993. DOI : 10.1002/chem.201501697

Access to New Endoperoxide Derivatives by Electrochemical Oxidation of Substituted 3-Azabicyclo[4.1.0]hept-4-enes.Nuter, F. ; Dimé, A.K.D. ; Chen, C. ; Bounaadja, L. ; Mouray, E. ; Florent, I. ; Six, Y.* ; Buriez, O.* ; Marinetti, A.* ; Voituriez, A.* Chem. Eur. J. 2015, 21, 5584-5593. DOI : 10.1002/chem.201406138

Self-Relay Gold(I)-Catalyzed Pictet-Spengler/Cyclization Cascade Reaction for the Rapid Elaboration of Pentacyclic Indole Derivatives. Gobé, V. ; Guinchard, X.* Chem. Eur. J. 2015, 21, 17587-17590. DOI : 10.1002/chem.201503941

When Phosphosugars Meet Gold : Synthesis and Catalytic Activities of Phostones and Polyhydroxylated Phosphonite Au(I) Complexes. Malik, G. ; Ferry, A. ; Guinchard, X.* Molecules 2015, 20, 21082-21093. Open-access article : DOI : doi:10.3390/molecules201219755

Stereoselective Synthesis of Chiral Polycyclic Indolic Architectures via Pd(0)-Catalysed Tandem Deprotection/Cyclization of Tetrahydro-β-carbolines on Allenes. Gobé, V. ; Guinchard, X.* Chem. Eur. J. 2015, 21, 8511-8520. DOI : 10.1002/chem.201500273

Phosphahelicenes in Asymmetric Organocatalysis : [3+2] Cyclizations of gamma-Substituted Allenes and Electron-Poor Olefins. Gicquel, M. ; Zhang, Y. ; Aillard, P. ; Retailleau, P. ; Voituriez, A.* ; Marinetti, A.* Angew. Chem. Int. Ed. 2015, 54, 5470-5473. DOI : 10.1002/anie.201500299

Catalytic Cyclization Reactions of Huisgen Zwitterion with α‑Ketoesters by in Situ Chemoselective Phosphine Oxide Reduction. Fourmy, K. ; Voituriez, A.* Org. Lett. 2015, 17, 1537-1540. DOI : 10.1021/acs.orglett.5b00426

2014

Planar Chiral Phosphoric Acids with Biphenylene-Tethered Paracyclophane Scaffolds : Synthesis, Characterization, and Catalytic Screening. Isaac, K. ; Stemper, J. ; Servajean, V. ; Retailleau, P. ; Pastor, J. ; Frison, G. ; Kaupmees, K. ; Leito, I. ; Betzer, J.-F.* ; Marinetti, A.* J. Org. Chem. 2014, 79, 9639-9646. DOI : 10.1021/jo501769t

Chiral Synthetic Equivalents of 2-Cyanoethyl Tetraisopropylphosphorodiamidite : Application to the Synthesis and Resolution of Chiral Phosphoric Acids. Isaac, K. ; Stemper, J. ; Retailleau, P. ; Betzer, J.-F.* ; Marinetti, A.* Eur. J. Org. Chem.2014, 4099-4106. DOI : 10.1002/ejoc.201402203

Domino Formation of Enamines – Intramolecular Cyclizations to 1-Aminotetralins from γ-Arylallene Aldehydes and Amines. Gobé, V. ; Retailleau, P. ; Guinchard, X.* Org. Lett. 2014, 16, 5438-5441. DOI : 10.1021/ol5026712

Thiophostone-Derived Brønsted Acids in the Organocatalyzed Transfer Hydrogenation of Quinolines : Influence of the P-Stereogenicity. Ferry, A. ; Stemper, J. ; Marinetti, A. ; Voituriez, A.* ; Guinchard, X.* Eur. J. Org. Chem. 2014, 188-193.DOI : 10.1002/ejoc.201301253

Helicenes with Embedded Phosphole Units in Enantioselective Gold Catalysis. Yavari, K. ; Aillard, P. ; Zhang, Y. ; Nuter, F. ; Retailleau, P. ; Voituriez, A.* ; Marinetti, A.* Angew. Chem. Int. Ed. 2014, 53, 861-865. DOI : 10.1002/anie.201308377

A [2+2+2] cyclization strategy for the synthesis of phosphorus embedding [6]helicene-like structures. Aillard P. ; Retailleau P. ; Voituriez A.* ; Marinetti, A.* Chem. Commun. 2014, 50, 2199-2201. DOI : 10.1039/C3CC48943D

Pd(0)-Catalyzed Tandem Deprotection/Cyclization of Tetrahydro-β-carbolines on Allenes : Application to the Synthesis of Indolo[2,3-a]quinolizidines. Gobé, V. ; Guinchard, X.* Org. Lett. 2014, 16, 1924-1927. DOI : 10.1021/ol500448j

Phospha-Thiahelicenes : Synthesis and Uses in Enantioselective Gold Catalysis. Aillard P. ; Voituriez, A.* ; Dova, D. ; Cauteruccio, S. ; Licandro, E.* ; Marinetti, A.* Chem. Eur. J. 2014, 20, 12373-12376. DOI : 10.1002/chem.201402822

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