Osipov Sergey Nikolaevich

D.Sc., Head of the Laboratory of Ecological Chemistry

Tel. 7-499-135-93-06, e-mail: .

 

Scientific interests:

Synthetic organic chemistry, metal catalysis, fluoroorganic chemistry, chemistry of biologically active compounds.

 

Main scientific achievments:

• New methodology for the synthesis of cyclic a-amino acids and their phosphorus analogs based on ring closing metathesis of diolefines and enynes under ruthenium catalysis has been developed.
• An efficient method for the preparation of 3-trifluoromethyl- and 3-difluoromethyl-thalidomides — analogs of drugs for treatment of painful inflammations associated with leprosy — has been elaborated.
• The first stereoselective synthesis of fluorinated bicyclo[3.1.0]hexane and [4.1.0]heptane aminoesters by ruthenium catalysed tandem addition of diazoalkane/cyclopropanation of enynes containing the fragment of a-CF₃-a-amino acid has been accomplished. This reaction is highly stereosective and leads to either Z- or E-configuration of the alkenyl chain, depending on the nature of the diazoalkane and reaction conditions.
• New synthetic pathway to unique trifluoromethyl substituted unsaturated systems: diolefins, enynes and allenynes has been developed. The method is based on [2,3]-sigmatropic rearrangement of allyl (or propargyl) group in trifluoromethyl-containing nitrogen and sulphur ylides in situ generated from the corresponding a-CF₃-a-diazocarboxylate and phosphonate under Cu-catalysis.
• A number of noval heterocyclic systems structurally resembled to some natural alkaloids has been obtained via metal-catalyzed carbocyclizations of fluorinated dienes, enynes and allenynes.

 

Some recent publications:

1.        M. Eckert, F. Monnier, G.T. Shchetnikov, I.D. Titanyuk, S.N. Osipov, S, Dérien, P.H. Dixneuf. Tandem catalytic carben addition/bicyclization of enynes. One-step synthesis of fluorinated bicyclic aminoesters by ruthenium catalysis, Org. Lett., 2005, 3741.

2.        D.V. Vorob’eva, I.D. Titanyuk, I.P. Beletskaya, S.N. Osipov. Synthesis of trifluoromethyl-containing depsipeptides via OH-insertion of rhodium carbenoid into carboxylic group of N-protected a-amino acids, Mendeleev Commun., 2005, 6, 222.

3.        I.D. Titanyuk, D.V. Vorob’eva, I.P. Beletskaya, S.N. Osipov, 1-Trifluoromethyl-1-diethoxyphosphoryl Carbene - New Synthon for the Preparation of CF₃-Containing a-Hydroxy and a-Amino Phosphonic Acid Derivatives, Synlett, 2006, 1355.

4.        H. Skarpos, D. V. Vorob’eva, S. N. Osipov, I.L. Odinets, E. Breuer, G.-V. Roeschenthaler, A simple Pathway to N-Oxalyl and N-Phosphonoformyl Derivatives of a-Tfm a-Amino Acids, Org. Biomol. Chem, 2006, 4, 3669.

5.        H. Skarpos, S.N. Osipov, D.V. Vorob’eva, I.L. Odinets, E. Lork, G.-V. R.oschenthaler, Synthesis of functionalized bisphosphonates via click chemistry, Org. Biomol. Chem., 2007, 5, 2361.

6.        G.T. Shchetnikov, A.S. Peregudov, S.N. Osipov, Effective pathway to the a-CF₃-substituted azahistidine analogues, Synlett, 2007, 1, 136.

7.        I.D. Titanyuk, I.P. Beletskaya, A.S. Peregudov, S.N. Osipov, Trifluoromethylated cyclopropanes and epoxides from CuI-mediated transformations of α-trifluoromethyl-diazophosphonate, J. Fluorine Chemistry, 2007, 128, 723.

8.        A.A. Semioshkin, S.N. Osipov, J.N. Grebenyuk, E.A. Nizhnik, I.A. Godovikov, G.T. Shchetnikov, V.I. Bregadze, An Effective Approach to 1,2,3-Triazole Containing 12-Vertex closo-Dodecaborates, Coll. Czech. Chem. Commun, 2007, 72(12), 1717.

9.        G.T. Shchetnikov, S.N. Osipov, C. Bruneau, P.H. Dixneuf, Ruthenium-catalyzed cyclotrimerization of 1,6- and 1,7-azadiynes: New access to fluorinated bicyclic amino acids, Synlett, 2008, 4, 578.

10.    O.I. Artyushin, D.V. Vorob’eva, T.P. Vasil’eva, S.N. Osipov, G.-V. Roeschenthaler, I.L. Odinets. Facile synthesis of phosphorylated azides in ionic liquids and their application for 1,2,3-triazoles preparation, Heteroatom. Chem., 2008, 3, 293.

11.    I.L. Odinets, E.V. Matveeva, E. V.Sharova, O. I.Artyushin, V.A.Kozlov, D.V. Vorob’eva, S.N. Osipov, T.A. Mastryukova, G.-V. Röschenthaler, Advantages of organophosphorus synthesis in ionic liquids:“green” approaches to useful phosphorus substituted building-blocks, Phosphorus, Sulfur, Silicon and Related Elements, 2008, 183(2), 38-49.

12.    O.I. Artyushin, S.N. Osipov, G.-V. Röschenthaler, I.L. Odinets, Propargyl substituted phosphonocarboxylates. Efficient synthesis and application for click chemistry, Synthesis, 2009, 21, 3579-3588.

13.    D.V. Vorobyeva, N.M. Karimova, T.P. Vasilyeva, G.T. Shchetnikov, S.N. Osipov, I.L. Odinets, G.-V. Röschenthaler, Synthesis of functionalized a-CF₃-a-aminophosphonates via Cu(I)-catalyzed 1,3-dipolar cycloaddition, J. Fluorine Chem., 2010, 131(3), 378-389.

14.    G.T. Shchetnikov, M.A. Zotova, C. Bruneau, P.H. Dixneuf, Synthesis of α-alkynyl-β,β,β-trifluoroalanine derivatives by Sonogashira cross-coupling reaction, Eur. J. Org. Chem., 2010, 1587.

15.    X. Miao, A. Blokhin, A. Pasynskii, S. Nefedov, S.N. Osipov, T. Roisnel, C. Bruneau, P.H. Dixneuf, Alkylidene-Ruthenium-Tin Catalysts for the Formation of Fatty Nitriles and Esters via Cross-Metathesis of Plant Oil Derivatives, Organometallics, 2010, 29 (21), 5257.