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.

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

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2024

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Reactivity and Steric Parameters from 2D to 3D Bulky Pyridines : Increasing Steric Demand at Nitrogen with Chiral Azatriptycenes Bensaida, A; Mahaut, D.; Tumanov, N.; Wouters, J.; Champagne, B.; Vanthuyne, N.; Robiette, R.; Berionni, G.* Angew. Chem. Int.Ed. 2024, 63, e202407503.

Regulating Nitrogen Ylides P-N bonds Reactivity Through Geometric Constraints with Cage-Shaped Triarylphosphines Hu, L.; Chakraborty, S.; Tumanov, N.; Wouters, J.; Robiette, R.;* Berionni, G.* Chem. Comm. 2024, 60, 7073-7076. In the top 25% downloaded ChemComm articles in July 2024

One-Carbon Homologation of Knoevenagel Adducts: Enantioselective Access to Benzhydryl Derivatives Janssens, J.; De Roose, M.; Jacquemin, A.; Vanhosmael, T.; Delbrassinne, A.; Collard, L.; Robiette, R.* J. Org. Chem.2024, 89, 7270-7274.

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.

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2023

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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.

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2022

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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.

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2021

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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.

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2020

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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.

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2019

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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

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.

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2018

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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.

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.

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.

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.

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.

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2017

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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.

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.

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.

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2016

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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.

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

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.

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

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.

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2015

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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.

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.

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.

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2014

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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.

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

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.

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2013

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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.

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.

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2012

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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.

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2011

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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.

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2010

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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.

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2009

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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

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2008

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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

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2007

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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.

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2006

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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.

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2005

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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.

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2004

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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.

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2003

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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.

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2002

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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.

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2001

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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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