D.Sc., Head of the laboratory for Homolytic Reactions of Organoelement Compounds

tel.: 7-499-135-50-33; Fax: 7-499-135-50-85; E-mail:

 

 

 

 

Research interests:

• asymmetric formation of C-C bond using transition metal complexes
• asymmetric synthesis in phase transfer catalysis and on the surface of the adsorbent
• use of catalytic processes in the synthesis of optically active compounds
• chemical-enzymatic synthesis and reactions catalyzed by enzymes in low water organic media
• stoichiometric asymmetric synthesis of amino acids using transition metal complexes
• studying the reactions of formation of carbon - an element in the redox reactions catalyzed by metals in low oxidation
• study the processes of chiral recognition in solution nonracemic mixtures of enantiomers
• preparation of biologically active additives to increase resistance of organisms

 

Main scientific achievements:

Developed a chemical-enzymatic method for producing a series of enantiomerically pure protogenic and nonprotogenic amino acids, ethambutol, and venlafaxine. Asymmetric transformation of racemic substrate to predominantly (S)-enantiomer via a combination of enzymatic hydrolysis and racemization.
Elaboration of the general method for the asymmetric synthesis of (R)- or (S)-α-amino acids via alkylation of the chiral Ni(II) Schiff base complexes of Gly.

A new type of efficient catalysts (alkoxides of chiral diols and amino alcohols) for the asymmetric alkylation of CH-acids under phase transfer catalysis.
An efficient catalytic method for asymmetric synthesis of a wide range of α -amino acids by alkylation of Schiff base glycine esters in the presence of (R)- or (S)- alkoxide of a chiral amino alcohol under phase transfer catalysis. The method is efficient for the synthesis of both enantiomers of short ¹¹C labeled α -amino acids. Due to the high positive nonlinear effect the skalemic catalyst (40% ee) was used without reducing the observed asymmetric induction (>90% ee).

First enantiopure phosphapalladacycle bearing asymmetric carbon directly bonded to palladium as the sole chirality source was synthesized. The preparation of the first optically active PC-palladacycle with a phosphorus atom in an axially chiral environment was realized.

A general method for obtaining of new previously unknown structural analogues (hydroxydiamines and triamines) of anti-tuberculosis drug ethambutol based on the available pirazolidines was elaborated.

 

Most important publications (more then 150, including 5 reviews ):

1. K.A.Kochetkov, V.M.Belikov. Asymmetric synthesis of amino acids, Uspechi Khimii, 1987, 56, 1832 [Russ. Chem. Rev., 1987, 56 (Engl. Transl.)].
2. К.А.Коchetkov, A.F.Sviridov. Stereoselective synthesis of amino acids from sugar, Bioorg. Khim., 1991, 5; Ibid., p. 149; Ibid., p. 293 [Russ. J. Bioorg. Chem., 1991 (Engl. Transl.)] (reviews).
3. Y.N.Belokon, V.I.Bakhmutov, N.I.Chernoglazova, K.A.Kochetkov, S.V.Vitt, N.S.Garbalinskaya, V.M.Belikov. General Method for the Asymmetric Synthesis of Amino Acids via Alkylation of the Chiral Ni(II) Schiff Base Complexes of Gly and Ala, J. Chem. Soc. Perkin Trans I, 1988, 305.
4. V.S.Parmar, A.Singh, K.S.Bisht, Y.N.Belokon, K.A.Kochetkov, N.S.Ikonnikov, S.A.Orlova, V.I.Tararov, T.F.Savelґeva. Schiff’s Bases of Amino Acid Esters as New Substrates for the Enantioselective Enzymatic Hydrolysis and Accompanied Asymmetric Transformations in Aqueous Organic Solvents, J. Org. Chem., 1996, 61, 1223.
5. Y.N.Belokon, K.A.Kochetkov, T.D.Churkina, N.S.Ikonnikov, A.A.Chesnokov, O.V.Larionov, V.S.Parmar, R.Kumar, H.B.Kagan. Asymmetric PTC C-alkylation Mediated by TADDOL - Novel Route to Enantiomerically Enriched a-Alkyl-a-Amino Acids, Tetrahedron: Asymmetry, 1998, 9, 851.
6. Y.N.Belokon, K.A.Kochetkov, T.D.Churkina, N.S.Ikonnikov, S.Viscochil, H.B.Kagan. Asymmetric PTC C-alkylation Mediated by NOBIN - Novel Route to Enantiomerically Enriched a-Amino Acids, Tetrahedron: Asymmetry, 1999, 10, 1723.
7. Y.N.Belokon, K.A.Kochetkov, V.I.Lozinsky, F.M.Plieva, N.S.Ikonnikov, V.I.Maleev, V.S.Parmar, R.Kumar. Enantioselective Hydrolysis of a Schiff’s Base of D,L-Phe-OEt in Water-poor Media Through the Reaction Catalyzed with a-Chymotrypsin Immobilized Within Hydrophilic Gel Supports. Appl. Biochem. & Biotechnol., 2000, 88, 97.
8. A.Markvicheva, S.V.Kuptsova, T.Yu.Mareeva, A.A.Vikhrov, T.N.Dugina, S.M.Strukova, Y.N.Belokon, K.A.Kochetkov, E.N.Baranova, D. Poncelet, V.Parmar, R.Kumar, V.P.Zubov, D.Rumsh. Immobilized Enzymes and Cell in Poly(N-vinyl caprolactam)-based Hydrogels: Preparation, Properties and Applications in Biotechnology, Appl. Biochem. & Biotechnol., 2000, 88, 145.
9. S.V.Kuptsova, E.A.Markvicheva, K.A.Kochetkov, Y.N.Belokon, D.Rumsh, V.P.Zubov. Proteases entrapted in hydrogels based on poly(N-vinyl caprolactam) as promising biocatalysts in water/organic systems, Biocatalysis and Biotransformations, 2000, 18, 133.
10. A.Singh, A.K.Prasad, W.Errington, Y.N.Belokon, K.A.Kochetkov, R.K.Saxena, S.C.Jain, V.S.Parmar. Synthetic and biotransformations studies on prochiral non-proteinogenic amino acids: diethyl a-acetamido, a-alkylmalonates, Indian J. Chem., 2000, 39B, 10.
11. Y.N.Belokon, K.A.Kochetkov, T.D.Churkina, N.S.Ikonnikov, A.A.Chesnokov, O.V.Larionov, I. Singh, V.S.Parmar, S.Viscochil, H.B.Kagan. Asymmetric PTC C-Alkylation Catalyzed by Chiral Derivatives of Tartaric Acid and Aminophenols. Synthesis of (R)- and (S)-a-Methyl Amino Acids. J. Organic Chem., 2000, 65, 7041.
12. Y.N.Belokon, K.A.Kochetkov, N.S.Ikonnikov, T.V.Strelkova, S.Haruruian, A. S. Sagian. New Preparative Synthesis of Enantiomerically Pure syn-(S)-b-Hydroxy-a-Amino Acids via Asymmetric Aldol Reactions of Aldehydes with Chiral Ni(II)-Complex of a Schiff’s Base of (S)-BPB and Glycine. Tetrahedron: Asymmetry, 2001, 12, 481.
13. Y.N.Belokon, K.A.Kochetkov, T.D.Churkina, N.S.Ikonnikov, O.V.Larionov, S.Haruruian, M.Nort, S.Viscochil, H.B.Kagan. Highly Efficient Phase Transfer Quickly Catalytic Synthesis of a-Amino Acids Based on a Novel Catalyst/Substrate Pair, Angew. Chem. Int. Ed., 2001, 40, 1948.
14. Y.N. Belokon, K.A. Kochetkov, T.D. Churkina, N.V. Bespalova, V.V. Prisyazhnyuk, O.V. Larionov, P. Kočovsky, Š.Vyskočil, S.Harutjunan, M.North, H. Kagan, M.Ezernitskaya, A.Peregudov, D.Seebach. Achiral Ni(II) Complexes of Schiff’s Bases of Glycine and N-(2’-benzoylphenyl)pyridine-2-carbamide or N-(2’-formylphenyl)-2-carbamide as Novel Substrates for the General Synthesis of Achiral, and Asymmetric Synthesis of Chiral α-Amino Acids with Novel Chiral PTC Catalysts, J. Am. Chem. Soc., 2003, 125, No.42, 12860.
15. O.V. Larionov, T.F.Savel’eva, K.A.Kochetkov, N.S.Ikonnikov, S.I.Kozhushkov, D.S. Yufit, J.A.K.Howard, V.N.Khrustalev, Y.N.Belokon, A.de Meijere, “Productive Asymmetric Synthesis of All Four Diastereomers of 3-(trans-2-Nitrocyclopropyl)alanine from Glycine with (S)- or (R)-2-[(N-benzylprolyl)amino]benzophenone as a Reusable Chiral Auxiliary”, Eur. J. Org. Chem., 2003, 869.
16. 16. A. Popkov, J. Sopková, I. Císaшová, J. Jirman, A. Lyиka, K.A. Kochetkov, “Stochiometric asymmetric synthesis of (S)-2-amino-3-(naphtalen-1-yl)propionic acid via chiral nickel complex. Crystal structure, circular dichroism, 1H-NMR and 13C-NMR spectra of the complex”, J.Coll. Czech. Chem. Comm., 2005, 70, 1397-1410.
17. P.B. Terent’ev, L.A.Sviridova, A.N.Tavtorkin, I.F.Lesheva, N.G.Kolotirkina, K.A. Kochetkov, «Regioselektive synthesis of 3- and 5- Pyrazoline derivatives. 1. Synthesis of Pyrazoline ketones», Chem.Heter.Comp (Rus), 2005, 1566-1572.
18. K.A. Kochetkov, А.B. Тerent’ev, Т.Т. Vasil’eva, О.V. Chahovskaya, N.Е. Mysova, H.H. Hambardzumyan, «Pentafluorophenyl carbonyl compounds in the Reformatsky-type reactions promoted with Fe(CO)₅-based metal complex systems», J. Fluorine Chem., 2008, 669 - 673.
19. L.A. Sviridova, G.A. Golubeva, A.N. Tavtorkin, K.A. Kochetkov, «Reductive amination of ketones with ammonia on the surface of an adsorbent», Mendeleev Commun. 2008, 258 - 259.
20. K.A. Kochetkov, L.A. Sviridova, G.A. Golubeva, A.N. Tavtorkin, « A new method for the Synthesis of Pyrazolidines with N-Amino Acid Substitutents», Chem.Heter.Comp (Rus), 2008, (3), 474 — 475.
21. 21. L.A. Sviridova, A.N. Tavtorkin, K.A. Kochetkov, «The new method for the  diastereoselective synthesis of pyrazolidines with N-and C-amino acid sustitutents», Amino acids, 2009, 37, S.1, Р. 125.
22. 22. V.V. Dunina, P.A. Zykov, M.V. Livantsov, I.V. Glukhov, K.A. Kochetkov, I.P. Gloriozov, Y.K. Grishin. ²First Optically Active Phosphapallada­cyc­le Bearing a Phosphorus Atom in an Axially Chiral Environment.² Organometallics, 2009, 28, 425-432.
23. K.A. Kochetkov, M.A. Galkina, O.M. Galkin, ”Enzymatic resolution of venlafaxine enantiomers”, Mendeleev Comm., 2010, 20, №11, 314-315.
24. O.V. Gorunova, P.A. Zykov, M.V. Livantsov, K.A. Kochetkov, Y.K. Grishin V.V. Dunina, ” Efficient catalysis of Suzuki reaction with cyclopalladated N,N-dimethyl­aminomethylferrocene under mild conditions”. Izvestia RAS, ser. Chim, (Rus), 2010, № 9, 1791-1793.
25. T.T. Vasil’eva, A.A. Ambartsumyan, O.V. Chakhovskaya, K.A. Kochetkov, “Ionic Liquids in Barbier–Zaitsev Reaction. Synthesis of 1-(Perfluorophenyl)-2-phenylethanol in the Presence of Iron Pentacarbonyl”, Zh. Organich. Khimii(Rus), 2010, 46, N 5, 643−645. (Russ. J. Org. Chem.,2010,46,N 5, 631−633, Engl Trans.)
26. V.V. Dunina, O.V. Gorunova, P.A. Zykov, K.A. Kochetkov, «Pallada­cyc­les in enantioselective catalysis», Uspechi. Khimii, 2011, 80, №1, 53-76. [Russ. Chem. Rev., 2011, №1, (Engl. Transl.)].
27. V.V. Dunina, O.N. Gorunova, P.A. Zykov, M.V. Livantsov, Y.K. Grishin, K.A. Kochetkov, A.V. Churakov, L.G. Kuz’mina, “First enantiopure phosphapalladacycle bearing asymmetric carbon directly bonded to palladium as the sole chirality source”, Polyhedron, , 2011, 30 (1), 27-32.