2010-2002

2010

1. Highly Diastereoselective alfa-Hydroxylation of Fox Chiral Auxiliary-Based Amide Enolates with Molecular Oxygen, Lubin, H. ; Tessier, A. ; Chaume, G. ; Pytkowicz, J. ; Brigaud, T. Org. Lett. 2010, 12, 1496-1499.

2. Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines, Chaume, G. ; Barbeau, O. ; Lesot, P. ; Brigaud, T. J. Org. Chem. 2010, 75, 4135-4145.

3. Straightforward synthesis of enantiopure (R)- and (S)-trifluoroalaninol, Pytkowicz, J. ; Stephany, O. ; Marinkovic, S. ; Inagaki, S. ; Brigaud, T. Org. Biomol. Chem. 2010, 8, 4540-4542
.Graphical abstract: Straightforward synthesis of enantiopure (R)- and (S)-trifluoroalaninol

4. Posttranslationally modified peptides efficiently mimicking neoantigens : a challenge for theragnostics of autoimmune diseases, Nuti, F.; Peroni, E.; Real-Fernandez, F.; Bonache, M. A.; Le Chevalier-Isaad, A.; Chelli, M.; Lubin-Germain, N.; Uziel, J.; Rovero, P.; Lolli, F.; Papini, A. M. Biopolymers 2010, 94, 791-799.

5. Synthesis of alkynes and alkynyl iodides bearing a protected amino alcohol moiety as functionalized amino acids precursors, Ayed, C.; Picard, J.; Lubin-Germain, N.; Uziel, J.; Auge, J. Sci. China Chem. 2010, 53, 1921-1926.

6. Indium-mediated alkynylation of sugars : synthesis of C-glycosyl compounds bearing a protected amino alcohol moiety, Ayed, C.; Palmier, S.; Lubin-Germain, N.; Uziel, J.; Auge, J. Carbohydr. Res. 2010, 345, 2566-2570. 

2009

1. Asymmetric aldol reactions using chiral CF3-Oxazolidines (Fox) as chiral auxiliary,Tessier, A. ; Pytkowicz, J. ; Brigaud, T. J. Fluorine Chem., 2009, 130, 1140-1144

2. Iodocyclization of Chiral CF3-Allylmorpholinones : A Versatile Strategy for the Synthesis of Enantiopure alfa-Tfm-Prolines and alfa-Tfm-Dihydroxyprolines, Caupène, C. ; Chaume, G. ; Ricard, L. ; Brigaud, T. Org. Lett. 2009, 11, 209-212

3. Convenient Synthesis of N-Terminal Tfm-Dipeptides from Unprotected Enantiopure alfa-Tfm-Proline and alfa-Tfm-Alanine, Chaume, G. ; Lensen, N. ; Caupène, C. ; Brigaud, T. Eur. J. Org. Chem. 2009, 33, 5717-5724

4. Huisgen Cycloaddition Reaction of C-Alkynyl Ribosides under Micellar Catalysis : Synthesis of Ribavirin Analogues, Youcef, R. A. ; Dos Santos, M. ; Roussel, S. ; Baltaze, J. -P. ; Lubin-Germain, N. ; Uziel, J. J. Org. Chem. 2009, 74, 4318-4323

5. Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis, Augé, J. ; Sizun, G. Green Chem. 2009, 11, 1179-1183
Graphical abstract: Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

2008

1. Umpolung reactivity of difluoroenol silyl ethers with amines and amino alcohols. Application to the synthesis of enantiopure alfa-difluoromethyl amines and amino acids, Huguenot, F. ; Billac, A. ; Brigaud, T. ; Portella, C. J. Org. Chem. 2008, 73, 2564-2569

2. Concise access to enantiopure (S)- and (R)-α-trifluoromethyl pyroglutamic acids from ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox), Chaume, G. ; Van Severen, M. -C. ; Ricard, L. ; Brigaud, T. J. Fluorine Chem. 2008, 129, 1104-1109

3. Fluorine••• and π•••Alcali Metal Interactions control in the Stereoselective Amide Enolates Alkylation using Fluorinated Oxazolidines (Fox) as Chiral Auxiliary : An Experimental and Theoretical Study, Sini, G. ; Tessier, A. ; Pytkowicz, J. ; Brigaud, T. Chem. Eur. J. 2008, 14, 3363-3370

4. Highly diastereoselective synthetic route to enantiopure β2-amino acids and γ-amino alcohols using a fluorinated oxazolidine (Fox) as chiral auxiliary, Tessier, A. ; Lahmar, N. ; Pytkowicz, J. ; Brigaud, T. J. Org. Chem. 2008, 73, 3970-3973

5. Direct C-glycosylation by indium-mediated alkynylation on sugar anomeric position, Lubin-Germain, N. ; Baltaze, J. -P. ; Coste, A. ; Hallonet, A. ; Lauréano, H. ; Legrave, G. ; Uziel, J. ; Augé, J. Org. Lett. 2008, 10, 725-728
Abstract Image

6. A new rationale of reaction metrics for green chemistry. Mathematical expression of the environmental impact chemical processes, Augé, J. Green Chem. 2008, 10, 225-231
Graphical abstract: A new rationale of reaction metrics for green chemistry. Mathematical expression of the environmental impact factor of chemical processes

7. Ferrocenyl Glycopeptides as Electrochemical Probes to Detect Autoantibodies in Multiple Sclerosis Patients’ Sera, Real Fernández, F. ; Chamois-Colson, A. ; Bayardon, J. ; Nuti, F. ; Peroni, E. ; Meunier-Prest, R. ; Lolli, F. ; Chelli, M. ; Darcel, C. ; Jugé, S. ; Papini, A. M. Pept. Science 2008, 90, 488-495

8. Design glycopeptides with different β-turn types as synthetic probes for the detection of autoantibodies of multiple sclerosis, Carotenuto, A. ; Alcaro, A. C. ; Saviello, M. R. ; Peroni, E. ; Nuti, F. ; Papini, A. M. ; Novellino, E. ; Rovero, P. J. Med. Chem. 2008, 51, 5304-5309

2007

1. The stereoselective synthesis of alfa-Tfm-amino acids from chiral CF3 building blocks, Brigaud, T. ; Chaume, G., Pytkowicz, J. ; Huguenot, F. Chim. Oggi 2007, 25(Supl), 8-10

2. Cyclic allyl carbamates in stereoselective syn SE’ processes : approach to sarcodictyins and eleutherobin, Dhulut, S. ; Bourin, A. ; Lannou, M.-I. ; Fleury, E. ; Lensen, N. ; Chelain, E. ; Pancrazi, A. ; Ardisson, J. ; Fahy, J. Eur. J. Org. Chem. 2007, 31, 5235-5243
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3. La chimie au coeur du développement durable : un message à faire passer dans l’enseignement et la société, Auge, J. L’Actual. Chim. 2007, 314, 44-50

4. Recent Advances in Indium-Promoted Organic Reactions, Auge, J. ; Lubin-Germain, N. ; Uziel, J. Synthesis 2007, 1739-1764

5. Ferrier-Type Alkynylation Reaction Mediated by Indium, Lubin-Germain, N. ; Hallonet, A. ; Huguenot, F. ; Palmier, S. ; Uziel, J. ; Auge, J. Org. Lett. 2007, 9, 3679-3682

2006-2002

1. Concise synthesis of enantiopure alfa-trifluoromethyl alanines, diamines and amino alcohols via the Strecker-type reaction, Huguenot, F. ; Brigaud, T. J. Org. Chem. 2006, 71, 7075-7078

2. Straightforward synthesis of (S)- and (R)-alfa-trifluoromethyl proline from chiral oxazolidines derived from ethyl trifluoropyruvate, Chaume, G., Van Severen, M.-C., Marinkovic, S. ; Brigaud, T. Org. Lett. 2006, 8, 6123-6126

3. Convenient asymmetric synthesis of beta-trifluoromethyl-beta-amino acid, beta-amino ketones and gama-amino alcohols via Reformatsky and Mannich type reactions from 2-trifluoromethyl-1,3-oxazolidines, Huguenot, F. ; Brigaud, T. J. Org. Chem. 2006, 71, 2159-2162

4. Chiral 2-trifluoromethyl-4-phenyloxazolidine : A novel highly performing chiral auxiliary for amides alkylation, Tessier, A. ; Pytkowicz, J. ; Brigaud, T. Angew. Chem. Int. Ed. Engl. 2006, 45, 3677-3681

5. Gram-Scale Preparation of a p-(C-Glucopyranosyl)-L-phenylalanine Derivative by a Negishi Cross-Coupling Reaction, Ousmer, M. ; Boucard, V. ; Lubin-Germain, N. ; Uziel J. ; Auge, J. Eur. J. Org. Chem. 2006, 1216-1221

6. Indium-Mediated Alkynylation in C-Glycoside Synthesis, Picard, J. ; Lubin-Germain, N. ; Uziel J. ; Auge, J. Synthesis 2006, 979-982

7. Mild synthesis of beta-amino-alfa,alfa-difluoroketones from acylsilanes and trifluoromethyltrimethylsilane in a one-pot imino aldol reaction, Jonet, S. ; Cherouvrier, F. ; Brigaud, T. ; Portella, C. Eur. J. Org. Chem. 2005, 4304-4312
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8. Highly diastereoselective addition of organometallic reagents to a trifluoroacetaldehyde hydrazone derived from (R)-N-benzylphenylglycinol, Fries, S. ; Pytkowicz, J. ; Brigaud, T. Tetrahedron Lett. 2005, 46, 4761-4764

9. On-resin head-to-tail cyclization of cyclotetrapeptides : optimization of crucial parameters, Alcaro, M. C. ; Sabatino, G. ; Uziel, J. ; Chelli, M. ; Ginanneschi, M. ; Rovero, P. ; Papini, A. M. J. Pept. Sci. 2004, 10, 218

10. C-Glycosylated Phenylalanine Synthesis by Palladium-Catalyzed Cross-Coupling Reactions, Boucard, V. ; Larrieu, K. ; Lubin-Germain, N. ; Uziel, J. ; Augé, J. Synlett 2003, 1834-1837

11. An Alternative Procedure in the Takai Reaction Using Chromium(III) Chloride Hexahydrate as a Convenient Source of Chromium(II), Augé, J. ; Boucard, V. ; Gil, R. ; Lubin-Germain, N. ; Picard, J. ; Uziel, J. Synth. Commun. 2003, 33, 3733-3739

12. Indium-catalyzed Barbier allylation reaction, Augé, J. ; Lubin-Germain, N. ; Marque, S. ; Seghrouchni, L. J. Organomet. Chem. 2003, 679, 79-83

13. NMR enantiodifferentiation of triphenylphosphonium salts by chiral hexacoordinated phosphate anions, Hebbe, V. ; Londez, A. ; Goujon-Ginglinger, C. ; Meyer, F. ; Uziel, J. ; Jugé, S. ; Lacour, J. Tetrahedron Lett. 2003, 44, 2467-2471

14. Indium-mediated formation of propargyl ketones from aldehydes or acyl chlorides, Augé, J. ; Lubin-Germain, N. ; Seghrouchni, L. Tetrahedron Lett. 2003, 44, 819-821

 

15. Efficient synthesis of beta-halogeno protected -alanines and their beta-phosphonium derivatives, Meyer, F. ; Laaziri, A. ; Papini, A. M. ; Uziel, J. ; Jugé, S. Tetrahedron : Asym., 2003, 14, 2229-2238

 

16. Lewis acid activation of chiral 2-trifluoromethyl-1,3-oxazolidines. Application to the stereoselective synthesis of trifluoromethylated amines, alfa- and beta-amino acids, Lebouvier, N. ; Laroche, C. ; Huguenot, F. ; Brigaud, T. Tetrahedron Lett. 2002, 43, 2827-2830

 

17. Indium-mediated carbonyl alkynylation, Augé, J. ; Lubin-Germain, N. ; Seghrouchni, L. Tetrahedron Lett. 2002, 43, 5255-5256

 

18. A convenient solvent-free preparation of 1,3,5-trioxanes, Augé, J. ; Gil, R. Tetrahedron Lett. 2002, 43, 7919-7920

 

19. Diastereoselective Alkylation of Schiff Bases for the Synthesis of Lipidic Unnatural Fmoc-Protected alfa-Amino Acids, Papini, A. M. ; Nardi, E. ; Nuti, F. ; Uziel, J. ; Ginanneschi, M. ; Chelli, M. ; Brandi, A. Eur. J. Org. Chem. 2002, 2736-2741