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Raphaël Robiette

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Institute of Condensed Matter and Nanosciences

The Robiette Research Group

Research in Organic and Physical Organic Chemistry



Publications


This page lists our publications. Please contact me if you would like to be sent reprints of these articles.

orcidhttps://orcid.org/000-0002-3449-565X

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2024



Chiral Isochalcogenourea-Catalysed Enantioselective (4+2) Cycloadditions of Allenoates
Vogl, L. S.; Mayer, P.; Robiette, R.;* Waser, M.*
Angew. Chem. Int. Ed. 2024, 63, e202315345.



2023



One-Carbon Homologation of a,b-Unsaturated Aldehydes: Access to a-Tertiary b,g-Unsaturated Aldehydes
Delbrassinne, A.; Takam Mba, B.J.; Collard, L.; Robiette, R.*
Eur.J.Org.Chem. 2023, e202300765.


Thiol S- Conjugate Profiles: A Comparative Investigation on Dual Hop and Grape Must with Focus on Sulfanylalkyl Aldehydes and Acetates Adducts
Chenot, C.; Robiette, R.; Haest, S.; Collin, S.*
J. Am. Soc. Brew. 2022 83, 23-30.



2022



First evidence of the glutathione S-conjugate of 3-sulfanylheptanol in green malt: discrepancy with the ubiquitous 5- and 6-C analogues
Chenot, C.; Robiette, R.; Collin, S.*
J. Inst. Brew. 2022, 128, 43-51.



2021



Cycloaddition of cyclopropanes for the elaboration of medium-sized carbocycles
Caillé, J.;* Robiette, R.*
Org. Biomol. Chem. 2021,19, 57002-5724.


Divergent Rearrangements of Vinylcyclopropane into Skipped Diene and Cyclopentene: Mechanism, Scope and Limitations
Delbrassinne, A.; Richald, M.; Janssens, J.; Robiette, R.*
Eur. J.Org. Chem. 2021, 2862-2868.


Sterically Hindered Ortho-Substituted Phosphatriptycenes as Configurationally Stable P-Chirogenic Triarylphosphines
Hu, L.; Mahaut, D.; Tumanov, N.; Wouters, J.; Collard, L.; Robiette, R.;* Berionni, G.*
Dalton Trans. 2021, 50, 4772-4777.


A Modular, Low Footprint and Scalable Flow Platform for the Expedient ?-Aminohydroxylation of Enolizable Ketones
Horst Kassin, V.-E.; Morodo, R.; Toupy, T.; Jacquemin, I.; Van Hecke, K.; Robiette, R.; Monbaliu, J.-C. M.*
Green Chem. 2021, 23, 2336-2351.




2020



Beta-lactams to act on the endocannabinoid system
Morelle, A.; Caruano, J.; Feledziak, M.; Michaux, C.; Perpete, E. A.; Muccioli, G. G.; Marchand-Brynaert, J.; Robiette, R.*
Chimie Nouvelle 2020, 134, 41-49.




2019



Synthesis and characterization of a 5-membered ring cyclic hydroxylamine coupled to triphenylphosphonium to detect mitochondrial superoxide by EPR spectrometry
Scheinok, S.; Driesschaert, B.; d'Hose, D.; Sonveaux, P.; Robiette, R.; Gallez, B.*
Free Rad. Res., 2019, 1135-1143.


Complementary Synthetic Approaches toward 9-Phosphatriptycene and Structure–Reactivity Investigations of Its Association with Sterically Hindered Lewis Acids
Hu, L.; Mahaut, D.; Tumanov, N.; Wouters, J.; Robiette, R.;* Berionni, G.*
J. Org. Chem. 2019, 84, 11268-11274


Unexpected Vinylcyclopropane Rearrangement: New Strategies Toward Skipped Dienes using Sulfonium Ylides
Richald, M.; Delbrassinne, A.; Robiette, R.*
Eur. J. Org. Chem. 2019, 3779-3782

Abstract

First Evidence of the Cysteine and Glutathione Conjugates of 2 3-Sulfanylpentan-1-ol in Hop (Humulus lupulus L.)
Chenot, C.; Robiette, R.; Collin, S.*
J. Agr. Food Chem.. 2019, 67, 4002-4010.

Abstract



2018



Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis
Frédéric, C. J.-M.; Cornil, J.; Vandamme, M.; Dumitrescu, L.; Tikad, A.; Robiette, R.; Vincent, S.*
Org. Lett. 2018, 20, 6769-6773.

Abstract

Synthesis of Cyclic Organic Carbonates Using Atmospheric Pressure CO2 and Charge-Containing Thiourea Catalysts
Fan, Y.; Tiffner, M.; Schörgenhumer, J.; Robiette, R.; Waser, M.;* Kass S. R.*
J. Org. Chem. 2018, 83, 9991-10000.

Abstract

Asymmetric Sulfur Ylide Mediated Formal (4+1) Annulation Reaction: Scope and Mechanism
Clergue, S.; Rousseau, O.; Delaunay, T.; Dequirrez, G.; Tran, T.V.; El Aakchioui, S.; Barozzino-COnsiglio, G.; Robiette, R.*
Chem. Eur. J. 2018, 11417-11425.
Selected as Hot Paper.

Abstract

Syntheses of Highly-Functionalized Spirocyclohexenes by Formal (4+2)-Annulation of Arylidene Azlactones with Allenoates
Eitzinger, A.; Zielke, K.; Widhalm, M.; Robiette, R.;* Waser, M.*
Asian J. Org. Chem. 2018, 7, 1620-1625.

Abstract

Effective Antimalarial Activities of ?-Hydroxy Diynes Isolated from Ongokea gore
Ntumba, J. K.;* Tshiongo, C. M.; Mifundu, M. N.; Robiette, R.; Taba, K. M.*
Planta Med. 2018, 84, 806-812.




2017



Investigation of 2-Sulfanylethyl Acetate Cysteine-S-Conjugate as a Potential Precursor of Free Thiols in Beer
Kankolongo Cibaka, M.-L.; Hang Tran, T. T.; Gros, J.; Robiette, R.; Collin, S.*
J. Am. Soc. Brew. Chem. 2017, 3, 228-235.



On the Origin of the E/Z Selectivity in the Synthesis of Tetrasubstituted Olefins by Wittig Reaction of ?-FluoroPhosphonium Ylides: An Explanation for the Low Stereoselectivity Observed in Reactions of ?-Alkoxy Aldehydes
Depré, D.;* Vermeulen, W. A. A.; Lang, Y.; Dubois, J.; Vendevivere, J.; Vandermeersch, J.; Huang, L.; Robiette, R.*
Org. Lett. 2017, 19, 1414-1417.

Abstract

Physico-chemical properties of diacetylenic light fuel oil from Congolese oleaginous plant Ongokea gore (Hua) Pierre
Ntumba, J. K.;* Mulula, A.; Kashishi, K. T.; Mifundu, M. M.; Robiette, R.; Taba, K. M.
J. Appl. Chem. 2017, 23, ID 7176317.



Asymmetric synthesis of 2,3-dihydrobenzofurans via a (4+1) annulation between ammonium ylides and in situ generated ortho-quinone methides
Meisinger, N.; Roiser, L.; Monkowius, U.; Himmelsbach, M.; Robiette, R.;* Waser, M.*
Chem. Eur. J. 2017, 23, 5137-5142.

Abstract

On the Origin of the Stereoselectivity in Chiral Amide-Based Ammonium Ylide-Mediated Epoxidations
Novacek, J.; Robiette, R.; Waser, M.*
Monatshefte für Chemie 2017, 148, 77-81.

Abstract


2016



3-Sulfanyl-4-methylpentan-1-ol in Dry-Hopped Beers: First Evidence of Glutathione S-Conjugates in Hop (Humulus lupulus L.)
Kankolongo Cibaka, M.-L.; Decourrière, L.; Lorenzo-Alonso, C.-J.; Bodart, E.; Robiette, R.; Collin, S.*
J. Agric. Food Chem. 2016, 64, 8572-8582.

Abstract

Biologically Active ?-Lactams: Synthesis and Natural Sources
Caruano, J.; Muccioli, G. G.; Robiette, R.*
Org. Biomol. Chem. 2016, 10134-10156.

Abstract

Towards a General Understanding of Carbonyl-Stabilised Ammonium Ylide-Mediated Epoxidation Reactions
Novacek, J.; Roiser, L.; Zielke, K.; Robiette, R.;* Waser, M.*
Chem. Eur. J. 2016, 22, 11422-11428.

Abstract

Benzylic Ammonium Ylide-Mediated Epoxidations
Roiser, L.; Robiette, R.;* Waser, M.*
Synlett 2016, 27, 1963-1968.

Abstract


Activation of the SN2 Reaction by Adjacent ? Systems: The Critical Role of Electrostatic Interactions and of Dissociative Character
Robiette, R.;* Trieu-Van, T.; Aggarwal, V. K.;* Harvey, J. N.*
J. Am. Chem. Soc. 2016, 138, 734-737.
Among the most read articles of the month in Jan 2016.

JACS TOC



2015



Formal Asymmetric (4+1) Annulation Reaction between Sulfur Ylides and 1,3-Dienes
Rousseau, O.; Delaunay, T.; Dequirez, G.; Trieu-Van, T. Robeyns, K.; Robiette, R.*
Chem. Eur. J. 2015, 21, 12899-12902.

Graphical Abstract


Isolation of a Series of Fatty Acid Components of Ongokea Gore Seed (Isano) Oil and Their Detailed Structural Analysis
Ntumba, J. K.; Collard, L.; Taba, K. M.; Robiette, R.*
Lipids 2015, 50, 313-322.

Lipids abstract


Asymmetric Syntheses of Three-Membered Heterocycles Using Chiral Amide-Based Ammonium Ylides
Pichler, M.; Novacek, J.; Robiette, R.; Poscher, V.; Himmelsbach, M.; Monkowius, U.; Mûller, N.; Waser, M.*
Org. Biomol. Chem. 2015, 13, 2092-2099.

Abstract



2014



Ongokea Gore (isanic) oil: analysis of its chemical composition and its valorisation by derivatisation
Ntumba, J. K.; Taba, K. M.; Robiette, R.*
Chimie Nouvelle 2014, 117, 12-20.

abstract


Synthesis of Monosubstituted 1,1-Dicarbonyl Ester 1,3-Dienes
Rousseau, O.; Delaunay, T.; Robiette, R.*
Synlett 2014, 519.

Synlett abstract


Formation of four-membered heterocycles
Robiette, R.;* Marchand-Brynaert, J.
In Comprehensive Organic Synthesis, 2nd ed.; Molander, G.; Knochel, P. (Eds.); Elsevier 2014, Vol. 5, 85-128.


(S)-1-(Pent-4’-enoyl)-4-(hydroxymethyl)-azetidin-2-one derivatives as inhibitors of human fatty acid amide hydrolase (hFAAH): synthesis, biological evaluation and molecular modelling
Caruano, J.; Feledziak, M.; Labar, G.; Michaux, C.; Perpète, E. A.; Muccioli, G. G.; Robiette, R.; Marchand-Brynaert, J.*
J. Enz. Inhib. Med. Chem. 2014, 29, 654-662.

abstract



2013



Development of a regioselective N-methylation of (benz)imidazoles providing the more sterically hindered isomer
Van Den Berge, E.; Robiette, R.*
J. Org. Chem. 2013, 78, 12220-12223.


New 5-aryl-1H-imidazoles display in vitro antitumor activity against apoptosis-resistant cancer models, including melanomas, through mitochondrial targeting
Mathieu,V.;* Van Den Berge,E.; Ceusters, J.; Konopka, T.; Cops, A.; Bruyère, C.; Pirker, C.; Berger, W.; Trieu-Van,T.; Serteyn, D.; Kiss, R.; Robiette, R.*
J. Med. Chem. 2013, 56, 6626-6637.


Comprendre les réactions pour mieux les développer et les utiliser
Robiette, R.;* Caruano, J.; Rousseau, O.; Tran, T.-V.; Van Den Berge, E.
Chimie Nouvelle 2013, 113, 18-20.


On the Origin of E/Z Selectivity in the Modified Julia Olefination: Importance of the Elimination Step
Robiette, R.;* Pospíšil, J.*
Eur. J. Org. Chem. 2013, 836-840.


First evidence of the production of odorant polyfunctional thiols by bottle refermentation
Nizet, S.; Gros, J.; Peeters, F.; Chaumont, S.; Robiette, R.; Collin, S.*
J. Am. Soc. Brew. Chem. 2013, 15-22.

abstract


Polycyclic phosphonic acid derivatives obtained by a [4+2] cycloaddition strategy using phosphonodienes
Villemin, E.; Robeyns, K.; Robiette, R.; Herent, M.-F.; Marchand-Brynaert, J.*
Tetrahedron 2013, 69, 1138-1147.



2012



Configurationally stable tetrathiarylmethyl molecular propeller
Driesschaert, B.; Robiette, R.; Le Duff, C. S.; Collard, L.; Robeyns, K.; Gallez, B.; Marchand-Brynaert, J.*
Eur. J. Org. Chem. 2012, 6517-6525.
It was featured on the cover.


Julia-Kocienski reaction-based 1,3-diene synthesis: Aldehyde-dependent (E,E/E,Z)-selectivity
Billard, F.; Robiette, R.; Pospíšil, J.*
J. Org. Chem. 2012, 77, 6358-6364.
Highlighted on Organic Chemistry Portal


Laser control in open quantum systems: preliminary analysis toward the Cope rearrangement control in methyl-cyclopentadienylcarboxylate dimer
Dive, G.; Robiette, R.; Chenel, A.; Ndong, M.; Meier, C.; Desouter-Lecomte, M.*
Theor. Chem. Acc. 2012, 131, 1236.


Practical synthesis of b-oxo benzo[d]-thiazolyl sulfones: Scope and limitations
Pospíšil, J.;* Robiette, R.; Sato, H.; Debrus, K.
Org. Biomol. Chem. 2012, 10, 1225-1234.



2011



Planar Chirality of Imidazole-Containing Macrocycles - Understanding and Tuning Atropisomerism
Van Den Berge, E.; Pospíšil, J.; Tran, T.-V.; Collard, L.; Robiette R.*
Eur. J. Org. Chem. 2011, 6649-6655.


Novel phosphonated bicyclic frameworks from Diels-Alder reaction as chelating agents of di- and trivalent metal cations
Villemin, E.; Elias, B.; Robiette R.; Robeyns, K.; Herent, M.-F.; Habib-Jiwan, J.-L.; Marchand-Brynaert, J.*
Tetrahedron Lett. 2011, 52, 5140-5144.


Chiral Properties of Tetrathiatriarylmethyl Spin Probes
Driesschaert, B.; Robiette R.; Lucaccioni, F.; Gallez, B.; Marchand-Brynaert, J.*
Chem. Comm. 2011, 47, 4793-4795.



2010



A practical synthesis of 1,2-nitroamines by Michael addition of N-nucleophiles to nitroalkenes
Robiette R.;* Tran, T.-V.; Cordi, A.; Tinant, B.; Marchand-Brynaert, J.*
Synthesis 2010, 3138-3142.


Synthesis and Biological Evaluation of Novel Imidazole-Containing Macrocycles
Nshimyumukiza, P.; Van Den Berge, E.; Delest, B.; Mijatovic, T.; Kiss, R.; Marchand-Brynaert, J.; Robiette R.*
Tetrahedron 2010, 66, 4515-4520.


Engineering Solid-State Molecular Switches N-salicylidene N-Heterocycle Derivatives
Robert, F.; Naik, A.D.; Hidara, F.; Tinant, B.; Robiette, R.; Wouters, J.; Garcia Y.*
Eur. J. Org. Chem. 2010, 621-637.
It was featured on the cover.



2009



Insights into the Origin of Solid-State Photochromism and Thermochromism of N-salicylideneanils: The Intriguing Case of Aminopyridines
Robert, F.; Naik, A. D.; Tinant, B.; Robiette, R.; Garcia Y.*
Chem. Eur. J. 2009, 15, 4327-4342


(R)-4-phenyloxazolidin-2-thione: an efficient chiral auxiliary for [4+2] cycloaddition of 1-aminodiene and activated phosphonodienophiles
Monbaliu, J.-C.; Robiette, R.; Peeters, D.; Marchand-Brynaert, J.*
Tetrahedron Lett. 2009, 50, 1314-1317



2008



Divergent and regioselective synthesis of 2,3,4- and 2,3,5-trisubstituted imidazoles
Delest, B.; Nshimyumukiza, P.; Fasbender, O.; Marchand-Brynaert, J.; Tinant, B.; Darro, F.;* Robiette, R.*
J. Org. Chem. 2008, 73, 6816-6823.


Reactions of Silyl-Stabilized Sulfur Ylides with Organoboranes: Enantioselectivity, Mechanism, and Understanding
Howells, D.; Robiette, R.; Fang, G. Y.; Knowles, L. S.; Woodrow, M. D.; Harvey, J. N.;* Aggarwal, V. K.*
Org. Biomol. Chem. 2008, 6, 1185-1189.
It was featured on the cover.


Diastereoselective synthesis of vinylcyclopropanes from dienes and sulfur ylides
Robiette, R.;* Marchand-Brynaert, J.
Synlett 2008, 517-520.
Highlighted on Organic Chemistry Portal



2007



Mechanism of the Morita-Baylis-Hillman Reaction: A Computational Investigation
Robiette, R.; Aggarwal, V. K.;* Harvey, J. N.*
J. Am. Chem. Soc. 2007, 129, 15513-15525.
Among the most accessed articlesin Oct-Dec 2007.


A Stereoselective Approach to 1,3-Aminoalcohols Protected as Cyclic Carbamates: Kinetic versus Thermodynamic Control
Broustal, G.; Ariza,X.; Campagne, J.-M.;* Garcia, J.;* Georges,Y.; Marinetti, A.; Robiette, R.*
Eur. J. Org. Chem. 2007, 26, 4293-4297.
Highlighted in Chem. Eur. J.



2006


QM and QM/MM Studies of Selectivity in Organic and Bioorganic Chemistry
Harvey, J. N.;* Aggarwal, V. K.; Bathelt, C. M.; Carreón-Macedo, J.-L.; Gallagher, T. C.; Holzmann, N.; Mulholland A. J.; Robiette R.
J. Phys. Org. Chem., 2006, 19, 608 - 615.


Mechanism and Diastereoselectivity of Aziridine Formation from Sulfur Ylides and Imines: A Computational Study
Robiette, R.*
J. Org. Chem., 2006, 71, 2726 - 2734.


Reactivity and Selectivity in the Wittig Reaction: A Computational Study
Robiette, R.; Richardson, J.; Aggarwal, V. K.*; Harvey, J. N.*
J. Am. Chem. Soc., 2006, 128, 2394 - 2409.


Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes
Robiette, R.; Conza, M.; Aggarwal, V. K.*
Org. Biomol. Chem., 2006, 4, 621 - 623.


Highly Enantioselective Synthesis of Glycidic Amides Using Camphor-Derived Sulfonium Salts. Mechanism and Applications in Synthesis
Aggarwal, V. K.;* Fuentes, D.; Harvey, J. N.; Hynd. G.; Ohara, D.; Picoul, W.; Robiette, R.; Smith, C.; Vasse, J.-L.; Winn. C. L.
J. Am. Chem. Soc., 2006, 128, 2105 - 2114.


Is phenyl a good migrating group in the rearrangement of organoborates generated from sulfur ylides?
Robiette, R.; Fang.G. Y.; Harvey, J. N.;* Aggarwal, V. K.*
Chem. Comm., 2006, 741 - 743.



2005


On the Origin of High E Selectivity in the Wittig Reaction of Stabilized Ylides: Importance of Dipole-Dipole Interactions
Robiette, R.; Richardson, J.; Aggarwal, V. K.*; Harvey, J. N.*
J. Am. Chem. Soc., 2005, 127, 13468 - 13469.


On the Importance of Leaving Group Ability in Reaction of Ammonium, Oxonium, Phosphonium and Sulfonium Ylides
Aggarwal, V. K.;* Harvey, J. N.;* Robiette, R.
Angew. Chem., Int. Ed., 2005, 44, 5468 - 5471.


Highlighted as Hot Paper in Angewandte


Theoretical approach of steric effects in the Diels-Alder Reaction
Boulanger, M.-L.; Leyssens, T.; Robiette, R.; Peeters D.*
J. Mol. Struct. (THEOCHEM), 2005, 731, 101 - 106.


A novel strategy towards aminophosphonic derivatives based on the Diels-Alder cycloaddition: experimental and theoretical approaches
Robiette, R.; Defacqz, N.; Peeters, D.; Marchand-Brynaert, J.*
Current Org. Synth., 2005, 2, 453 - 477.



2004


Stereochemistry and conformation of amido-phosphono-cyclohexene derivatives, assigned by NMR and X-Ray diffraction analyses
Tinant, B.*; Defacqz, N.; Robiette, R.; Touillaux, R.; Marchand-Brynaert, J.
Phosphorus, Sulfur and Silicon and the Related Elements, 2004, 179, 389 - 402.



2003


Crystal structure of (S)-3-(Z-1',3'-butadienyl)-4-phenylthiazoline-2-one, C13H13NOS, a chiral 1-amino-diene useful in Diels-Alder cycloaddition reactions
Tinant, B.*; Robiette, R.; Marchand-Brynaert, J.
Z. Kristallogr. NCS, 2003, 218, 475 - 476.


Design of a New and Highly Effective Chiral Auxiliary for Diels-Alder Reaction of 1-Aminodiene
Robiette, R.; Cheboub-Benchaba, K.; Peeters, D.; Marchand-Brynaert, J.*
J. Org. Chem., 2003, 68, 9809 - 9812.


Analysis of electronic reorganisation in reaction molecules
Peeters, D.; Leyssens, T.; Robiette, R.
Chimie Nouvelle, 2003, 82, 91 - 95


[4+2] Cycloaddition of 1-Amidodienes and 2-Substituted Vinylphosphonates: Application to Asymmetric Synthesis of 3-Amino-5-phosphono-1-cyclohexene Derivatives
Robiette, R.; Defacqz, N.; Stofferis, J.; Marchand-Brynaert, J.*
Tetrahedron, 2003, 59, 4167 - 4175.


A Study of the rearrangement products of chiral alkylated 1,3-oxazolidine- and thiazolidine-2-thiones
Robiette, R.; Dekoker-Malengreau, A.; Marchand-Brynaert, J.*
Heterocycles, 2003, 60, 523 - 536.



2002


Influence of Diene Subtitution on Transition State Stabilization in Diels-Alder Reactions
Robiette, R.; Marchand-Brynaert, J.; Peeters, D.*
J. Org. Chem., 2002, 67, 6823 - 6826.


Theoretical Study of the Influence of Phosphonate Substituents on Diels-Alder Reactions
Robiette, R.; Marchand-Brynaert, J.; Peeters, D.*
J. Mol. Struct. (Theochem), 2002, 587, 159 - 169.



2001


Asymmetric synthesis of b- and g-amidophosphonates by Diels-Alder reaction using chiral amidodiene: theoretical and experimental study of the facial selectivity of chiral N-dienyl lactam
Robiette, R.; Marchand-Brynaert, J.*
J. Chem. Soc., Perkin Trans 2, 2001, 11, 2155 - 2158.


[4+2] Cycloaddition of phosphoryl-substituted dienes and dienophiles with a view of preparing aminophosphonic acid derivatives
Marchand-Brynaert, J.; Defacqz, N.; Robiette, R.
In Recent Res. Develop. In Org. Chem., 2001, Vol 5, 207 - 223.





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