CBL Chemical Biology Lab

Thierry Brigaud

Full Professor - Head of the Lab

Education & Career :

1990 : PhD in organic synthesis

University Claude Bernard, Lyon I. Nucleophilic fluorination in benzylic position or in a-position of a thioether (Advisor: Prof. E. Laurent)

1990-1991 : Post-doc position in Prof. I. Ojima’s Laboratory.

State University of New York at Stony Brook. Asymmetric synthesis of non-protein amino acids and their peptides - Asymmetric synthesis of fluorinated analogues of the taxol side chain.

1991- 2002 : Associate professor.

University of Reims-Champagne-Ardenne, Prof. C. Portella’s group. Mixte organofluorine –silicon – sulfur chemistry

2002- : Full professor.

University of Cergy-Pontoise. Direction of the organofluorine and asymmetric synthesis group in the SOSCO laboratory (now CBL).

 

Research Interests :

Chiral fluorinated compounds (amino acids, pseudopeptides, amino alcohols, diamines…)

Fluorinated peptides, fluorinated bioactive molecules.

Asymmetric synthesis – Fluorinated chiral auxiliaries

 

Recent Publications :

Incorporation of CF3−Pseudoprolines into Peptides: A Methodological Study, Chaume, G.; Simon, J.; Caupène, C.; Lensen, N.; Miclet, E.; Brigaud, T. J. Org. Chem. 2013, 78, 10144-10153.

Effects of enantiopure (S)-a-trifluoromethyl proline containing MIF-1’s analogue on stress-induced analgesia,Bocheva, A.; Nocheva, H.; Jlalia, I.; Lensen, N.; Chaume, G.; Brigaud, T. Med. Chem. 2013, 3, 206-209.

Synthesis of a MIF-1 analogue containing Enantiopure (S)-α-Trifluoromethyl Proline and Biological Evaluation on Nociception, Jlalia, I.; Lensen, N.; Chaume, G.; Dzhambazova, E.; Astasidi, L.; Hadjiolova, R.; Bocheva, A.; Brigaud, T. Eur. J. Med. Chem. 2013, 62, 122-129.

Conformational properties of peptides incorporating a fluorinated pseudoproline residue, Chaume, G.; Feytens, D.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Miclet, E. New J. Chem. 2013, 37, 1336-1342

Crystallization-Induced Dynamic Resolution of Fox Chiral Auxiliary and Application to the Diastereoselective Electrophilic Fluorination of Amide Enolates. Lubin, H.; Dupuis, C.; Pytkowicz, J.; Brigaud, T. J. Org. Chem., 2013, 78 (7), 3487-3492.

Local control of the cis-trans isomerization and backbone dihedral angles in peptides using trifluoromethylated pseudoprolines, Feytens, D.; Chaume, G.; Chassaing, G.; Lavielle, S.; Brigaud, T.; Byun, B. J.; Kang, Y. K.; Miclet, E. J. Phys. Chem. B 2012, 116, 4069-4079.

2-Trifluoromethyl-2-methyl-4-phenyloxazolidine: A new chiral auxiliary for highly diastereoselective enolate alkylation, Tessier, A.; Pytkowicz, J.; Brigaud, T. J Fluorine Chem. 2012, 134, 122-127

Highly Diastereoselective Synthesis of Enantiopure β-Trifluoromethyl β-Amino Alcohols from Chiral Trifluoromethyl Oxazolidines (Fox), Simon, J.; Chelain, E.; Brigaud, T. Org. Lett., 2012, 14 (2), 604–607

Synthesis of trifluoromethyl cyclohexyl, cyclohexenyl and aryl compounds via stepwise Robinson annulation, Massicot, F.; Iriarte, A. M.; Brigaud, T.; Lebrun, A.; Portella, C. Org. Biomol. Chem. 2011, 2, 600-603.

Concise Synthesis of Enantiopure (S)- and (R)-alpha-Trifluoromethyl Aspartic Acid and alpha-Trifluoromethyl Serine from Chiral Trifluoromethyl Oxazolidines (Fox) via the Strecker-type Reaction, Simon, J.; Nguyen, T. T.; Chelain, E.; Lensen, N.; Pytkowicz, J.; Chaume, G.; Brigaud, T. Tetrahedron : Asymmetry 2011, 22, 309-314.

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.

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.

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.

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

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

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

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

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

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

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

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

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

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

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

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