Institut de Chimie Moléculaire et des Matériaux d'Orsay

Chimie Peptidomimétique Photochimie et Procédés Alternatifs

Publications de l'équipe

2019

Synthesis of β-sulfinyl cyclobutane carboxylic amides via a formal α to β sulphoxide migration process. L. Ghisu, N. Melis, L. Serusi, A. Luridiana, F. Soddu, F. Secci, P. Caboni, R. Guillot, D. J. Aitken, A. Frongia, Org. Biomol. Chem., 2019

Identification of ion pairs in solution by IR spectroscopy: crucial contributions of gas phase data and simulations. S. Habka, T. Very, J. Donon, V. Vaquero-Vana, B. Tardivel, F. Charnay-Pouget, M. Mons, D. J. Aitken, V. Brenner, E. Gloaguen, Phys. Chem. Chem. Phys., 2019, 21, Accepted article

Reversal of Diastereoselectivity in a Masked Acyl Cyanide (MAC) Reaction: Synthesis of Protected erythro-β-Hydroxyaspartate Derivatives. M. Esgulian, M. Buchotte, R. Guillot, S. Deloisy, D. J. Aitken, Org. Lett., 2019, 21, 2378-2382

Brønsted acid catalysed synthesis of 3-(2-alkoxyethyl)indoles from α‐arylaminocyclobutanones and alcohols. L. Serusi, M. Bonnans, A. Luridiana, F. Secci, P. Caboni, T. Boddaert, D. J. Aitken, A. Frongia, Advanced Synthesis & Catalysis, 2019, 361, 1908-1912

A Selective Deprotection Strategy for the Construction of trans-2-Aminocyclopropanecarboxylic Acid Derived Peptides. T. Boddaert, J. E. Taylor, S. D. Bull, D. J. Aitken, Org. Lett., 2019, 21, 100-103

2018

Formation de liaisons Si-C pour la synthèse d'hétérocycles silylés. M. Durandetti, T. Boddaert, L'Actualité Chimique, 2018, 434, 11-18

Brønsted Acid Mediated Cascade Reaction to Access 3‑(2-Bromoethyl)benzofurans. S. Porcu, S. Demuro, A. Luridiana, A. Cocco, A. Frongia, D. J. Aitken, F. Charnay-Pouget, R. Guillot, G. Sarais, F. Secci, Org. Lett., 2018, 20, 7699-7702

Acid-catalyzed synthesis of functionalized arylthio cyclopropane carbaldehydes and ketones. S. Porcu, A. Luridiana, A. Martis, A. Frongia, G. Sarais, D. J. Aitken, T. Boddaert, R. Guillot, F. Secci, Chem. Commun., 2018, 54, 13547-13550

Fullerene Helical Peptide: Synthesis, Characterization and Formation of Self-Assembled Monolayers on gold surfaces. H. Nasrallah, J. Rabah, V. Bui-Thi-Tuyet, K. Baczko, H. Fensterbank, F. Bourdreux, A.-M. Goncalves, V. Declerck, S. Boujday, V. Humblot, K. Wright, A. Vallée, E. Allard, New J. Chem., 2018

Strategic C to N Replacement in β-Peptides: Atomic Level Control of Helical Folding. V. Declerck, D. J. Aitken, J. Org. Chem., 2018, 83, 8793-8800

A Greener and Efficient Method for Nucleophilic Aromatic Substitution of Nitrogen-Containing Fused Heterocycles. J. F. Campos, M. Loubidi, M.-C. Scherrmann, S. Berteina-Raboin, Molecules, 2018, 23, 684, 1-15

Preparation of cyclobutene acetals and tricyclic oxetanes via photochemical tandem and cascade reactions. J. Buendia, Z. Chang, H. Eijsberg, R. Guillot, A. Frongia, F. Secci, J. Xie, S. Robin, T. Boddaert, D. J. Aitken, Angewandte Chemie International Edition, 2018, 57, 6592-6596

Cooperative 5- and 10-membered ring interactions in the 10-helix folding of oxetin homo-oligomers. S. S. Ragab, A. F. Kassir, R. Guillot, M.-C. Scherrmann, T. Boddaert, D. J. Aitken, Chem. Commun., 2018, 54, 1968-1971

A Photochemical Route to 3- and 4-Hydroxy Derivatives of 2-Aminocyclobutane-1-carboxylic Acid with an all-cis Geometry. Z. Chang, F. Boyaud, R. Guillot, T. Boddaert, D. J. Aitken, Journal of Organic Chemistry, 2018, 83, 527-534

2017

Identification of insulin-sensitizing molecules acting by disrupting the interaction between the Insulin Receptor and Grb14. A. Gondoin, C. Hampe, R. Eudes, C. Fayolle, C. Pierre-Eugène, M. Miteva, B. O. Villoutreix, F. Charnay-Pouget, D. J. Aitken, T. Issad, A.-F. Burnol, Scientific Reports, 2017, 7, 16901

Acid-catalyzed reaction of 2-hydroxycyclobutanone with benzylic alcohols. A. Martis, A. Luridiana, A. Frongia, M. Arca, G. Sarais, D. J. Aitken, R. Guillot, F. Secci, Org. Biomol. Chem., 2017, 15, 10053-10063

Synthesis of 2,2-bis(pyridin-2-yl amino)cyclobutanols and their conversion into 5-(pyridin-2-ylamino)dihydrofuran-2(3H)-ones. L. Ghisu, N. Melis, F. Secci, P. Caboni, M. Arca, R. Guillot, T. Boddaert, D. J. Aitken, A. Frongia, Org. Biomol. Chem., 2017, 15, 9779-9784

β-Cyclodextrin-Mediated Enantioselective Photochemical Electrocyclization of 1,3-Dihydro-2H-azepin-2-one. A. T. Mansour, J. Buendia, J. Xie, F. Brisset, S. Robin, D. Naoufal, O. Yazbeck, D. J. Aitken, J. Org. Chem., 2017, 82, 9832-9836

Stereoselective and regioselective pinacol-type rearrangement of a fused bicyclic oxetanol scaffold. N. Melis, A. Luridiana, R. Guillot, F. Secci, A. Frongia, T. Boddaert, D. J. Aitken, European Journal of Organic Chemistry, 2017, 2017, Issue 39, 5896–5902

Conformational effects through hydrogen bonding in a constrained γ-peptide template: from intra-residue 7-membered rings to a gel-forming sheet structure. H. Awada, C. M. Grison, F. Charnay-Pouget, J.-P. Baltaze, F. Brisset, R. Guillot, S. Robin, A. Hachem, N. Jaber, D. Naoufal, O. Yazbeck, D. J. Aitken, J. Org. Chem., 2017, 82, 4819–4828

Studies on cyclization reactions of 3-amino-2,4-dihydroxybutanoic acid derivatives. M. Esgulian, V. Belot, R. Guillot, S. Deloisy, D. J. Aitken, Org. Biomol. Chem., 2017, 15, 1453-1462

2016

The weight of flash chromatography: A tool to predict its mass intensity from thin-layer chromatography. F. Pessel, J. Augé, I. Billault, M.-C. Scherrmann, Beilstein Journal of Organic Chemistry, 2016, 12, 2351–2357

Synthetic access to all four stereoisomers of oxetin. A. F. Kassir, S. S. Ragab, T. A. M. Nguyen, F. Charnay-Pouget, R. Guillot, M.-C. Scherrmann, T. Boddaert, D. J. Aitken, J. Org. Chem., 2016, 81, 9983-9991

Iodine-catalyzed formation of substituted 2-aminobenzothiazole derivatives in PEG400. G. Dumonteil, M.-A. Hiebel, M.-C. Scherrmann, S. Berteina-Raboin, RSC Advances, 2016, 6, 73517-73521

An α-Helix-Mimicking 12,13-Helix: Designed α/β/γ-Foldamers as Selective Inhibitors of Protein–Protein Interactions. C. M. Grison, J. A. Miles, S. Robin, A. J. Wilson, D. J. Aitken, Angewandte Chemie International Edition, 2016, 55, 11096-11100

Total synthesis of triazole-linked C-glycosyl flavonoids in alternative solvents and environmental assessment in terms of reaction, workup and purification. F. Pessel, I. Billault, M.-C. Scherrmann, Green Chem., 2016, 18, 5558-5568

Synthesis and antiproliferative activity of a natural like glycoconjugate polycyclic compound. B. Maggio, M. V. Raimondi, D. Raffa, F. Plescia, M.-C. Scherrmann, N. Prosa, M. Lauricella, A. D’Anneo, G. Daidone, European Journal of Medicinal Chemistry, 2016, 122, 247-256

13-Helix folding of a β/γ-peptide manifold designed from a "minimal-constraint" blueprint. C. M. Grison, S. Robin, D. J. Aitken, Chem. Commun., 2016, 52, 7802-7805

Deracemizing organocatalyzed Michael addition reactions of 2-(arylthio)cyclobutanones with β-nitrostyrenes. A. Luridiana, A. Frongia, D. J. Aitken, R. Guillot, G. Sarais, F. Secci, Org. Biomol. Chem., 2016, 14, 3394-3403

Thermodynamic and Structural Investigation of Synthetic Actinide–Peptide Scaffolds. S. Safi, A. Jeanson, J. Roques, P. L. Solari, F. Charnay-Pouget, C. Den Auwer, G. Creff, D. J. Aitken, E. Simoni, Inorg. Chem., 2016, 55, 877-886

2015

The leguminous species Anthyllis vulneraria as a Zn-hyperaccumulator and eco-Zn catalyst resources. C. M. Grison, M. Mazel, A. Sellini, V. Escande, J. Biton, C. Grison, Environmental Science and Pollution Research, 2015, 22, 5667-5676

Metallophytes for organic synthesis: towards new bio-based selective protection/deprotection procedures. C. M. Grison, A. Velati, V. Escande, C. Grison, Environmental Science and Pollution Research, 2015, 22, 5686-5698

Intrinsic Folding Proclivities in Cyclic β-Peptide Building Blocks: Configuration and Heteroatom Effects Analyzed by Conformer-Selective Spectroscopy and Quantum Chemistry. M. Alauddin, E. Gloaguen, V. Brenner, B. Tardivel, M. Mons, A. Zehnacker-Rentien, V. Declerck, D. J. Aitken, Chemistry – A European Journal, 2015, 21, 16479-16493

Enantioselective Organocatalyzed Desymmetrization of 3-Substituted Cyclobutanones through Michael Addition to Nitroalkenes. F. Capitta, A. Frongia, J. Ollivier, D. J. Aitken, F. Secci, P. P. Piras, R. Guillot, Synlett, 2015, 26, 123-126

Synthesis of functionalized tryptamines by Bronsted acid catalysed cascade reactions. N. Melis, F. Secci, T. Boddaert, D. J. Aitken, A. Frongia, Chem. Commun., 2015, 51, 15272-15275

The discovery of 9/8-ribbons, β/γ-peptides with curved shapes governed by a combined configuration-conformation code. C. M. Grison, S. Robin, D. J. Aitken, Chem. Commun., 2015, 51, 16233-16236

Fine Tuning of β-Peptide Foldamers: a Single Atom Replacement Holds Back the Switch from an 8-Helix to a 12-Helix. A. Altmayer-Henzien, V. Declerck, J. Farjon, D. Merlet, R. Guillot, D. J. Aitken, Angewandte Chemie International Edition, 2015, 54, 10807-10810

Catalytic Enantioselective Synthesis of α-(Benzylamino)cyclobutanones. N. Melis, L. Ghisu, R. Guillot, P. Caboni, F. Secci, D. J. Aitken, A. Frongia, European Journal of Organic Chemistry, 2015, 2015, 4358-4366

Cupreine grafted onto silica as an enantioselective and recyclable catalyst for the 1,4-addition of malonate to trans-β-nitrostyrene. I. Billault, R. Launez, M.-C. Scherrmann, RSC Advances, 2015, 5, 29386-29390

Investigation of the copper(I) catalysed azide-alkyne cycloaddition reactions (CuAAC) in molten PEG2000. I. Billault, F. Pessel, A. Petit, R. Turgis, M.-C. Scherrmann, New J. Chem., 2015, 39, 1986-1995

Pushing the limits of signal resolution to make coupling measurement easier. J. E. H. Pucheta, D. Pitoux, C. M. Grison, S. Robin, D. Merlet, D. J. Aitken, N. Giraud, J. Farjon, Chem Commun, 2015, 51, 7939-7942

Conformational preferences in the β-peptide oligomers of cis-2-amino-1-fluorocyclobutane-1-carboxylic acid. A. Hassoun, C. M. Grison, R. Guillot, T. Boddaert, D. J. Aitken, New J. Chem., 2015, 39, 3270-3279

2014

A simple synthesis of 2-keto-3-deoxy-D-erythro-hexonic acid isopropyl ester, a key sugar for the bacterial population living under metallic stress. C. M. Grison, B.-L. Renard, C. Grison, Bioorganic Chemistry, 2014, 52, 50-55

Direct Spectroscopic Evidence of Hyperconjugation Unveils the Conformational Landscape of Hydrazides. E. Gloaguen, V. Brenner, M. Alauddin, B. Tardivel, M. Mons, A. Zehnacker-Rentien, V. Declerck, D. J. Aitken, Angewandte Chemie International Edition, 2014, 53, 13756-13759

Recent Progress in the Synthetic Assembly of 2-Cyclopentenones. D. J. Aitken, H. Eijsberg, A. Frongia, J. Ollivier, P. P. Piras, Synthesis, 2014, 46, 1-24

Catalytic Enantioselective Synthesis of α-Arylaminocyclobutanones. D. J. Aitken, P. Caboni, H. Eijsberg, A. Frongia, R. Guillot, J. Ollivier, P. P. Piras, F. Secci, Adv. Synth. Catal., 2014, 356, 941-945

Straightforward Synthesis of Various 2,3-Diarylimidazo[1,2-α]pyridines in PEG400 Medium through One-Pot Condensation and C–H Arylation. M.-A. Hiebel, Y. Fall, M.-C. Scherrmann, S. Berteina-Raboin, European Journal of Organic Chemistry, 2014, 2014, 4643-4650

Stereoselective intermolecular [2 + 2]-photocycloaddition reactions of maleic anhydride: stereocontrolled and regiocontrolled access to 1,2,3-trifunctionalized cyclobutanes. F. Hernvann, G. Rasore, V. Declerck, D. J. Aitken, Org. Biomol. Chem., 2014, 12, 8212-8222

Practical Syntheses of Both Enantiomers of the Conformationally Restricted GABA Analogue cis-(2-Aminocyclobutyl)acetic Acid. H. Awada, S. Robin, R. Guillot, O. Yazbeck, D. Naoufal, N. Jaber, A. Hachem, D. J. Aitken, European Journal of Organic Chemistry, 2014, 2014, 7148-7155

2013

Reactivity of 1-aminoazetidine-2-carboxylic acid during peptide forming procedures: observation of an unusual variant of the hydrazino turn. A. Altmayer-Henzien, V. Declerck, R. Guillot, D. J. Aitken, Tetrahedron Letters, 2013, 54, 802-805

A unified synthesis of all stereoisomers of 2-(aminomethyl)cyclobutane-1-carboxylic acid. V. André, M. Gras, H. Awada, R. Guillot, S. Robin, D. J. Aitken, Tetrahedron, 2013, 69, 3571-3576

Molecular structures of the photodimers of 5-phenyluracil and 6-phenyluracil. A. Vidal, R. Paugam, R. Guillot, S. Faure, E. Pereira, D. J. Aitken, Tetrahedron Letters, 2013, 54, 2536-2537

Photochemical transformation of a 1,2-dihydropyridin-3-one: an original tandem retro-[4+2]/[2+2] cycloaddition process. D. J. Aitken, A. Frongia, X. Gaucher, J. Ollivier, H. Rafique, C. Sambiagio, F. Secci, Tetrahedron Letters, 2013, 54, 2825-2827

Total synthesis of high loading capacity PEG-based supports: evaluation and improvement of the process by use of ultrafiltration and PEG as a solvent. R. Turgis, I. Billault, S. Acherar, J. Auge, M.-C. Scherrmann, Green Chem., 2013, 15, 1016-1029

An unusual and diastereoselective rearrangement during an intramolecular ene reaction involving a disilane. A. Giros, R. Guillot, L. Blanco, S. Deloisy, Eur. J. Org. Chem., 2013, 5809-5813

Regioselective preparation of 7-oxanorborna-2,5-diene-2,3-dicarboxylic acid derivatives by the Diels-Alder reaction: a selective access to furans by retro-Diels-Alder reaction. N. Sultan, R. Guillot, L. Blanco, S. Deloisy, Synthesis, 2013, 45, 2018-2028

29Si-1H IMPACT HMBC: a suitable tool for analyzing silylated derivatives. J. Farjon, A. Giros, S. Deloisy, L. Blanco, J. Hannedouche, E. Schulz, D. Merlet, Magnetic Resonance in Chemistry, 2013, 51, 230-233

Solution State Conformational Preferences of Dipeptides Derived from N-Aminoazetidinecarboxylic Acid: An Assessment of the Hydrazino Turn. A. Altmayer-Henzien, V. Declerck, D. Merlet, J.-P. Baltaze, J. Farjon, R. Guillot, D. J. Aitken, Journal of Organic Chemistry, 2013, 78, 6031-6039

Fast-pulsing NMR techniques for the detection of weak interactions: successful natural abundance probe of hydrogen bonds in peptides. A. Altmayer-Henzien, V. Declerck, D. J. Aitken, E. Lescop, D. Merlet, J. Farjon, Organic & Biomolecular Chemistry, 2013, 11, 7611-7615

SENSASS NMR: New NMR techniques for enhancing the sensitivity and the spectral resolution of polymer supported chemicals. N. Prosa, M.-C. Scherrmann, D. Merlet, J. Farjon, Journal of Magnetic Resonance, 2013, 237, 63-72