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Oleg Kulinkovich

https://etis.ee/CV/Oleg_Kulinkovich/est
11.05.1948
6202818
o.kulinkovich@gmail.com

Teenistuskäik

Töökohad ja ametid
26.11.2010–28.02.2013   
Tallinna Tehnikaülikool, Matemaatika-loodusteaduskond, Keemiainstituut, Orgaanilise keemia õppetool, külalisprofessor (1,00)
01.01.1989–31.12.2010   
Valgevene Riiklik Ülikool, professor
 
 
Haridustee
1971–1975   
Aspirantuur, Valgevene Riiklik Ülikool
1966–1971   
Valgevene Riiklik Ülikool
 
 
Teadusorganisatsiooniline ja -administratiivne tegevus
1991−2010   
Organometallsünteesi laboratooriumi Juhataja
1989−1991   
Orgaanilise keemia professor
1976−1989   
Orgaanilise keemia dotsent
 
 
Loometöö
Organometallsüntees, väikeste tsüklite keemia, asümmeetriline süntees, looduslike ja bioaktiivsete ühendite süntees

Kvalifikatsioon

Teaduskraadid
Oleg Kulinkovich, doktorikraad, 1987, (juh) , Активированные циклопропилкетоны: методы получения, свойства и практическое применение, Belarussian State University Minsk.
Oleg Kulinkovich, doktorikraad, 1975, (juh) , Циклоприсоединение дизлоркарбена к винилацетиленовым углеводородам (Diklorokarbeeni tsükloliitumine vinüülatsetüleensetele ühenditele), Valgevene Riiklik Ülikool.
 
 
Teadustöö põhisuunad
ETIS KLASSIFIKAATOR: 4. Loodusteadused ja tehnika; 4.11. Keemia ja keemiatehnika; CERCS KLASSIFIKAATOR: P390 Orgaaniline keemia

Publikatsioonid

Klass
Aasta
Publikatsioon
 
1.1.
2011
Kovalenko, V.N., Kulinkovich, O.G. (2011). The resolution of trans-2,2-dichloro-3-methylcyclopropanecarboxylic acid via crystallization of its salts with (+)- and (-)-α-phenylethylamine, and the transformation of the resulting enantiomers into (R)- and (S)-dimethyl 2-methylsuccinates. Tetrahedron-Asymmetry, 22 (1), 26−30.10.1016/j.tetasy.2010.12.014.
1.1.
2010
Mineyeva, I.V.; Kulinkovich, O.G. (2010). Methyl 3-bromomethyl-3-butenoate as an isopentane building block for the stereoselective preparation of (S)-4-methyl-3,6-dihydro-2H-pyran-2-carbaldehyde and (+)-faranal. Tetrahedron Letters, 51 (14), 1836−1839.10.1016/j.tetlet.2010.01.120.
1.1.
2010
Hurski, A.L.; Kulinkovich, O.G. (2010). Total synthesis of epothilone D by sixfold ring cleavage of cyclopropanol intermediates. Tetrahedron Letters, 51 (27), 3497−3500.10.1016/j.tetlet.2010.04.109.
1.1.
2010
Kovalenko, V.N.; Sokolov, N.A.; Kulinkovich, O.G. (2010). Synthesis of epothilones molecule fragment (15R)-C13-C 21 from D-mannitol. Russian Journal of Organic Chemistry, 46 (11), 1702−1708.10.1134/S1070428010110175.
1.1.
2010
Kananovich, D.G.; Zubrytski, D.M.; Kulinkovich, O.G. (2010). A Convenient Transformation of 2-Alkylidenecycloalkanones into Alkyl-Substituted Bicyclo[n.1.0]alkan-1-ols: Application to the Synthesis of Capsaicin. Synlett, 2010 (7), 1043−1046.10.1055/s-0029-1219568.
1.1.
2009
Hurski, A.L.; Sokolov, N.A.; Kulinkovich, O.G. (2009). A cyclopropanol approach to the synthesis of both enantiomers of the C13-C21 fragment of epothilones. Tetrahedron, 65 (17), 3518−3524 . DOI: 10.1016/j.tet.2009.02.003.
1.1.
2009
Kovalenko, V.N.; Masalov, N.V.; Kulinkovich, O.G. (2009). Synthesis of (+)-disparlure from diethyl (-)-malate via opening and fragmentation of the three-membered ring in tertiary cyclopropanols. Russian Journal of Organic Chemistry, 45 (9), 1318−1324 . DOI: 10.1134/S1070428009090036.
1.1.
2009
Mineeva, I.V.; Kulinkovich, O.G. (2009). Preparation of 3-bromomethyl-3-butenal diethylacetal and its conversion into isoprenoid aldehydes derivatives. Russian Journal of Organic Chemistry, 45 (11), 1623−1632. DOI: 10.1134/S1070428009110086.
1.1.
2008
Isakov, V.E.; Kulinkovich, O.G. (2008). Highly stereoselective allylic ethylation with alkoxytitanacyclopropane reagents. Synthesis of (1R/S,7R)-1,7-dimethylnonyl propanoate, the Western corn rootworm sex attractant. Tetrahedron Letters, 49 (49), 6959−6961 . DOI: 10.1016/j.tetlet.2008.08.063.
1.1.
2008
Kulinkovich, O.G.; Isakov, V.E.; Kananovich, D.G. (2008). Stereocontrolled alkylation of unsaturated compounds with alkoxytitanacyclopropane reagents. The Chemical Record, 8 (5), 269−278. DOI: 10.1002/tcr.20155.
1.1.
2008
Kananovich, D.G.; Kulinkovich, O.G. (2008). Studies on the origin of cis-diastereoselectivity of the titanium-mediated cyclopropanation of carboxylic esters with Grignard reagents. Stereochemistry of the intramolecular cyclization of β-metalloketones. Tetrahedron, 64 (7), 1536−1547. DOI: 10.1016/j.tet.2007.10.075.
1.1.
2007
Kananovich, D.G.; Hurski, A.L.; Kulinkovich, O.G. (2007). A highly stereoselective transformation of carboxylic esters to trisubstituted olefins via cationic cyclopropyl–allyl rearrangement of sulfonates of cis-1,2-disubstituted cyclopropanols. Tetrahedron Letters, 48 (48), 8424−8429. DOI: 10.1016/j.tetlet.2007.09.172.
1.1.
2007
Kulinkovich, O.G.; Kananovich, D.G. (2007). Advanced Procedure for the Preparation of cis-1,2-Dialkylcyclopropanols – Modified Ate Complex Mechanism for Titanium-Mediated Cyclopropanation of Carboxylic Esters with Grignard Reagents. European Journal of Organic Chemistry, 2007 (13), 2121−2132. DOI: 10.1002/ejoc.200601035.
1.1.
2006
Matyushenkov, E.A.; Kulinkovich, O.G. (2006). Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone. Russian Journal of Organic Chemistry, 42 (4), 491−495 . DOI: 10.1134/S1070428006040038.
1.1.
2006
Bekish, A.V.; Prokhorevich, K.N.; Pritytskaya, T.S.; Kulinkovich, O.G. (2006). Recent development of the cyclopropanol methodology for the preparation of methyl or methylene branched natural compounds. Polish Journal of Chemistry, 80 (4), 549−558 .
1.1.
2006
Kulinkovich, O.G.; Shevchuk, T.A.; Isakov, V.E.; Prokhorevich, K.N. (2006). Reductive ethylation of homoallyl alcohols with a disubstituted double bond with ethylmagnesium bromide in the presence of titanium(IV) isopropoxide. Russian Journal of Organic Chemistry, 42 (5), 659−664 . DOI: 10.1134/S1070428006050034.
1.1.
2006
Astashko, D.A.; Kulinkovich, O.G.; Tyvorskii, V.I. (2006). Synthesis of isomeric 1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonanes and 1′-hydroxybrevicomin from ethyl 5-oxohexenoate ethyleneacetal through cyclopropanation of an ester group followed by oxidative opening of the three-membered ring. Russian Journal of Organic Chemistry, 42 (5), 719−723 . DOI: 10.1134/S1070428006050125.
1.1.
2006
Bekish, A.V.; Prokhorevich, K.N.; Kulinkovich, O.G. (2006). Transformation of esters into 2-substituted allyl halides via tertiary cyclopropanols: Application in the stereoselective synthesis of (2S,3S,7S)-3,7-dimethyl-2-pentadecyl acetate, the sex pheromone of the pine sawfly Neodiprion sertifer. European Journal of Organic Chemistry, 22, 5069−5075 . DOI: 10.1002/ejoc.200600481.
1.1.
2006
Prokhorevich, K.N.; Kulinkovich, O.G. (2006). The synthesis of the insect pheromone (2S,3R,7R)-3,7-dimethyltridec-2-yl acetate from racemic 3,4-dimethyl-γ-butyrolactone by diastereoselective chiral resolution. Tetrahedron-Asymmetry, 17 (21), 2976−2980 . DOI: 10.1016/j.tetasy.2006.11.005.
1.1.
2006
Churykau, D.H.; Kulinkovich, O.G. (2006). A convenient procedure for transformation of tertiary cyclopropanols into 5-substituted isoxazoles. Synlett, 20, 3427−3430 . DOI: 10.1055/s-2006-956475.
1.1.
2005
Lysenko, I.L.;, Kulinkovich, O.G. (2005). Stereoselective synthesis of (7aS)-1-methylenehexahydro-1H-pyrrolizine and (-)-heliotridane from N-diphenylmethyl-(S)-proline ethyl ester. Russian Journal of Organic Chemistry, 41 (1), 70−74 .
1.1.
2005
Kulinkovich, O.G.; Kozyrkov, Y.Y.; Bekish, A.V.; Matiushenkov, E.A.; Lysenko, I.L. (2005). A convenient way for the conversion of carboxylic esters into 2-substituted allyl halides. Synthesis, 10, 1713−1717 . DOI: 10.1055/s-2004-834869.
1.1.
2005
Bekish, A.V.; Kulinkovich, O.G. (2005). Differentiation between the ethoxycarbonyl groups in diethyl malate via their titanium-catalyzed reductive cyclopropanation with ethylmagnesium bromide and subsequent site-selective three-carbon ring cleavage. Tetrahedron Letters, 46 (41), 6975−6978 . DOI: 10.1016/j.tetlet.2005.08.076.
1.1.
2005
Bekish, A.V.; Isakov, V.E.; Kulinkovich, O.G. (2005). A cyclopropanol approach to the synthesis of the C13-C21 fragment of epothilones from diethyl (S)-malate. Tetrahedron Letters, 46 (41), 6979−6981 . DOI: 10.1016/j.tetlet.2005.08.075.
1.1.
2004
Kozyrkov, Y.Yu.; Kulinkovich, O.G. (2004). A Convenient and Stereoselective Method for the Preparation of 2-Substituted 1,3-Alkadienes from 1,2-Disubstituted Cyclopropanols. Synlett, 2, 344−346 . DOI: 10.1055/s-2003-44987.
1.1.
2004
Tyvorskii, V.I.; Astashko, D.A.; Kulinkovich, O.G. (2004). A convenient route to 1-(2-oxiranyl)-1,4-diketones and their application to the synthesis of endo-brevicomin, endo-isobrevicomin, frontalin and related compounds via alkylated 6,8-dioxabicyclo[3.2.1]octan-2-ones. Tetrahedron, 60 (7), 1473−1479 . DOI: 10.1016/j.tet.2003.12.027.
1.1.
2004
Kulinkovich, O.G. (2004). Alkylation of carboxylic acid derivatives with dialkoxytitanacyclopropane reagents. Russian Chemical Bulletin, 53 (5), 1065−1086 .
1.1.
2004
Bekish, A.V.; Prokhorevich, K.N.; Kulinkovich, O.G. (2004). Transformation of esters into allyl halides via substituted cyclopropanols. Application in the synthesis of (2S,3R,7R/S)-3,7-dimethyltridec-2-yl acetate and propionate, sex attractants of pine sawfly Diprion pini. Tetrahedron Letters, 45 (27), 5253−5255 . DOI: 10.1016/j.tetlet.2004.05.022.
1.1.
2004
Churykau, D.H.; Zinovich, V.G.; Kulinkovich, O.G. (2004). A convenient and chemoselective method for the reductive ring cleavage of isoxazoles and isoxazolines with EtMgBr/Ti(Oi-Pr)4 reagent. Synlett, 11, 1949−1952 . DOI: 10.1055/s-2004-831294.
1.1.
2004
Kulinkovich, O. (2004). Synthetic applications of intermolecular cyclopropanation of carboxylic esters with dialkoxytitanacyclopropane reagents. European Journal of Organic Chemistry, 22, 4517−4529 . DOI: 10.1002/ejoc.200400234.
1.1.
2003
Matyushenkov, E.A.; Churikov, D.G.; Sokolov, N.A.; Kulinkovich, O.G. (2003). Ethylation of 2-Alkenyltetrahydrofurans and 2-Alkenyltetrahydropyrans Catalyzed by Titaniun(IV) Isoprpopoxide. Supplement to the Synthesis of Pheromones of Lesser Plum Worm and Tea Leaf Roller Moth. Russian Journal of Organic Chemistry, 39 (4), 478−485 .
1.1.
2003
Kulinkovich, O.G. (2003). The chemistry of cyclopropanols. Chemical Reviews, 103 (7), 2597−2632 . DOI: 10.1021/cr010012i.
1.1.
2003
Isakov, V.E.; Kulinkovich, O.G. (2003). The head-to-head reductive coupling of homoallylic alcohols promoted by titanium(II)-olefin complexes. Synlett, 7, 967−970 .
1.1.
2003
Raiman, M.V.; Pukin, A.V.; Tyvorskii, V.I.; De Kimpe, N.; Kulinkovich, O.G. (2003). A convenient approach to the synthesis of 2-(2-aminoethyl)pyrroles and their heterocyclization into hydrogenated pyrrolopyridines and related pyrroloindolizines. Tetrahedron, 59 (28), 5265−5272. DOI: 10.1016/S0040-4020(03)00777-4.
1.1.
2002
Kozyrkov, Y.Yu.; Kulinkovich, O.G. (2002). A simple and efficient conversion of tertiary cyclopropanols to 2-substituted allyl halides. Synlett, 3, 443−446 .
1.1.
2002
Verniest, G.; Bombeke, F.; Kulinkovich, O.G.; De Kimpe, N. (2002). Stereoselective synthesis of cis-2-aryl- and 2-alkyl-1-chlorocyclopropanecarboxaldehydes. Tetrahedron Letters, 43 (4), 599−602 .
1.1.
2002
Racouchot, S.; Sylvestre, I.; Ollivier, J.; Kozyrkov, Y.; Pukin, A.; Kulinkovich, O.; Salaün, J. (2002). Titanium-mediated diastereoselective formation of (E)- or (Z)-2-substituted 1-vinylcyclopropanols: Scope and limitation, applications. European Journal of Organic Chemistry, 13, 2160−2176 .
1.1.
2002
Lysenko, I.L.; Bekish, A.V.; Kulinkovich, O.G. (2002). Stereoelective conversion of ethyl pipecolinate into (±)-α- and (±)-β-conhydrins. Russian Journal of Organic Chemistry, 38 (6), 875−879 .
1.1.
2001
Kulinkovich, O.G.; Epstein, O.L.; Isakov, V.E.; Khmel'nitskaya, E.A. (2001). Regioselective carbon-carbon bond formation in titanium mediated reaction of ethylmagnesium bromide with allylic alcohols and allylic ethers. Synlett, 1, 49−52 .
1.1.
2001
Kulinkovich, O.G.; Astashko, D.A.; Tyvorskii, V.I.; Ilyina, N.A. (2001). Synthesis of α,β-epoxy ketones from alkyl- and arylsubstituted cyclopropanols. Synthesis, 10, 1453−1455 .
1.1.
2001
Aelterman, W.; De Kimpe, N.; Tyvorskii, V.; Kulinkovich, O. (2001). Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions. Journal of Organic Chemistry, 66 (1), 53−58 .
1.1.
2001
Tyvorskii, V.I.; Bobrov, D.N.; Kulinkovich, O.G.; Tehrani, K.A.; Kimpe, N.D. (2001). Synthesis of 5-alkyl-4-amino-2-(trifluoromethyl)pyridines and their transformation into trifluoromethylated 1H-pyrazolo[4,3-c]pyridines. Tetrahedron, 57 (10), 2051−2055 .
1.1.
2001
Lysenko, I.L.; Kulinkovich, O.G. (2001). A convenient procedure for preparation of 1-(1-aminoalkyl)-1-cyclopropanols from N-benzyl α-amino acid esters. Russian Journal of Organic Chemistry, 37 (9), 1238−1243 .
1.1.
2001
Epstein, O.L.; Kulinkovich, O.G. (2001). Two-step synthesis of (±)-stigmolone, the pheromone of Stigmatella aurantiaca. Tetrahedron Letters, 42 (22), 3757−3758 .
1.1.
2000
Nevar, N.M.; Kel'in, A.V.; Kulinkovich, O.G. (2000). One step preparation of 1,4-diketones from methyl ketones and α-bromomethyl ketones in the presence of ZnCl2·t-BuOH·Et2NR as a condensation agent. Synthesis, 9, 1259−1262 .
1.1.
2000
Shevchuk, T.A.; Kulinkovich, O.G. (2000). Convenient preparation of 2-substituted cyclobutanones from esters of 2-alkoxyalkanoic acids. Russian Journal of Organic Chemistry, 36 (4), 491−495 .
1.1.
2000
Shevchuk, T.A.; Kulinkovich, O.G. (2000). 58 Preparation of branched ketones from esters via 1,2-disubstituted cyclopropanols. Synthesis of methylenomycin B. Russian Journal of Organic Chemistry, 36 (8), 1124−1126 .
1.1.
2000
Kulinkovich, O.G.; De Meijere, A. (2000). 1,n-Dicarbanionic titanium intermediates from monocarbanionic organometallics and their application in organic synthesis. Chemical Reviews, 100 (8), 2789−2834 . DOI: 10.1021/cr980046z.
1.1.
2000
Kozyrkov, Y.Yu.; Pukin, A.; Kulinkovich, O.G.; Ollivier, J.; Salaun, J. (2000). A convenient approach to substituted 1-(1-alkenyl)cyclopropanols: A new preparation of 2,3-methanoamino acids. Tetrahedron Letters, 41 (33), 6399−6402 .
1.1.
2000
Tyvorskii, V.I.; Bobrov, D.N.; Kulinkovich, O.G.; Aelterman, W.; Kimpe, N.D. (2000). Synthesis of 3-(trifluoromethyl)benzo[c][1,6]naphthyridines from substituted 4H-pyran-4-ones via 4-amino-5-aryl-2-(trifluoromethyl)pyridines. Tetrahedron, 56 (37), 7313−7318 .
1.1.
2000
Epstein, O.L.; Savchenko, A.I.; Kulinkovich, O.G. (2000). On the mechanism of titanium-catalyzed cyclopropanation of esters with aliphatic organomagnesium compounds. Deuterium distribution in the reaction products of (CD3)2CHMgBr with ethyl 3-chloropropionate in the presence of titanium tetraisopropoxide. Russian Chemical Bulletin, 49 (2), 378−380 .
1.1.
2000
Kulinkovich, O.G. (2000). Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds. Pure and Applied Chemistry, 72 (9), 1715−1719 .
1.2.
2000
Bagutsky, V.V.; Kulinkovich, O.G. (2000). Synthesis of substituted 5H-1,2,3,4,6,7,8,9-octahydrodipyrido-[4,3-b;3′,4′-d]pyrroles by the Pictet-Spengler condensation. Chemistry of Heterocyclic Compounds, 36 (5), 537−541 . DOI: 10.1007/BF02290840.
15.05.2019

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SFSF0140060s12Katalüütilise asümmeetriline sünteesi ja stereokeemilise analüüsi meetodid ja rakendused 01.01.201231.12.2013Margus LoppTallinna Tehnikaülikool, Matemaatika-loodusteaduskond285 640,00 EUR
SFSF0142725s06Uued asümmeetrilise sünteesi strateegiad ja meetodid01.01.200631.12.2011Margus LoppTallinna Tehnikaülikool, Matemaatika-loodusteaduskond749 371,30 EUR