Collect. Czech. Chem. Commun. 2005, 70, 1397-1410
https://doi.org/10.1135/cccc20051397

Asymmetric Synthesis of (S)-2-Amino-3-(1-naphthyl)propanoic Acid via Chiral Nickel Complex. Crystal Structure, Circular Dichroism, 1H and 13C NMR Spectra of the Complex

Alexander Popkova,*, Ivana Císařováb, Jana Sopkovác, Josef Jirmand, Antonín Lyčkae and Konstantin A. Kochetkovf,*

a Faculty of Health and Social Studies, University of South Bohemia, 370 01 České Budějovice, Czech Republic
b Department of Inorganic Chemistry, Faculty of Natural Sciences, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic
c UFR des Sciences Pharmaceutiques, 5 rue Vaubénard, 14032 Caen, France
d Research Institute for Pharmacy and Biochemistry, U Kabelovny 130, 102 37 Prague 10, Czech Republic
e Research Institute for Organic Syntheses, Rybitví 296, 532 18 Pardubice 20, Czech Republic
f A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 117813 Moscow, Russia

Individual author index pages


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    1996, Vol. 61, Issue 7, pp. 1109–1114 [Abstract]
  • Martin Doležal, Jiří Hartl, Antonín Lyčka, Vladimír Buchta and Želmíra Odlerová
    Synthesis and Antituberculotic Properties of Some Substituted Pyrazinecarbothioamides
    1996, Vol. 61, Issue 7, pp. 1102–1108 [Abstract]
  • Jiří Vohlídal, Jaromír Plešek, Jan Sedláček, Ivana Císařová, Pavel Matějka and Stanislav Heřmánek
    Cobaltacarboranylacetylene 8,8'-(μ-CHC-CH2S)-(1,2-C2B9H10)2-3-Co(III): Synthesis, Characterization and Polymerization of New Substituted Acetylene
    1996, Vol. 61, Issue 6, pp. 877–887 [Abstract]
  • Václav Všetečka, Ivana Císařová and Jaroslav Podlaha
    Conformation of Methylsulfonyl Group: A Comparison of the Data for 2-Chlorophenyl Methyl Sulfone in Solution and in Crystal
    1996, Vol. 61, Issue 5, pp. 733–741 [Abstract]
  • Jaroslav Podlaha, Ivana Císařová, Martin Bělohradský and Jiří Závada
    Crystal and Molecular Structure of cis-2,2',3',2"-Tetraacetoxy-1,1':4',1"-ternaphthyl
    1996, Vol. 61, Issue 5, pp. 726–732 [Abstract]
  • Antonín Lyčka
    1H, 13C and 15N NMR Spectra of Coupling Products of Benzenediazonium Salts with Aliphatic Nitro Compounds and Study of Their E/Z Isomerism
    1996, Vol. 61, Issue 4, pp. 589–596 [Abstract]
  • Roman Řeřicha, Ivana Císařová and Jaroslav Podlaha
    Crystal and Molecular Structure of Lithium Benzohydroxamate-Benzohydroxamic Acid (1 : 1) Adduct
    1996, Vol. 61, Issue 1, pp. 139–146 [Abstract]
  • Vladimír Pejchal, Jaroslav Holeček, Milan Nádvorník and Antonín Lyčka
    13C and 119Sn NMR Spectra of Some Mono-n-butyltin(IV) Compounds
    1995, Vol. 60, Issue 9, pp. 1492–1501 [Abstract]
  • Pavel Hradil and Josef Jirman
    Synthesis of 2-Aryl-3-hydroxyquinolin-4(1H)-ones
    1995, Vol. 60, Issue 8, pp. 1357–1366 [Abstract]
  • Martin Doležal, Jiří Hartl, Antonín Lyčka, Vladimír Buchta and Želmíra Odlerová
    Synthesis and Antituberculotic Activity of Some Substituted 3-Arylamino-5-cyano-2-pyrazinecarboxamides
    1995, Vol. 60, Issue 7, pp. 1236–1241 [Abstract]
  • Josef Jirman and Alexander Popkov
    1H, 13C, and 15N NMR Spectra of Ni(II) Complexes of Schiff Bases of (S)-2-(N-Benzylprolyl)aminobenzophenone and α-Monosubstituted Glycine and Determination of Configuration of the Complexes by 2D NOESY Spectra
    1995, Vol. 60, Issue 6, pp. 990–998 [Abstract]
  • Ivana Císařová, Jana Podlahová and Jaroslav Podlaha
    Crystal Structure of the Adduct Hexahydroxotelluric Acid-Disodium Ethylenediaminetetraacetate-Water (1/1/2)
    1995, Vol. 60, Issue 5, pp. 820–828 [Abstract]
  • Jaromír Toman, Jaromír Mindl, Antonín Lyčka, Jiří Klicnar, Ivana Srovnalová and Miloš Koníček
    Structure of Reaction Products of Some Substituted Quinoxaline N-Oxides with Carbanions
    1994, Vol. 59, Issue 11, pp. 2493–2500 [Abstract]
  • Josef Jirman* and Alexander Popkov
    1H, 13C and 15N NMR Spectra of Ni(II) Complex of Schiff Base from (S)-2-(N-Benzylprolyl)amino-5-methylbenzophenone and Glycine
    1994, Vol. 59, Issue 9, pp. 2103–2108 [Abstract]
  • Karel Handlíř, Antonín Lyčka, Jaroslav Holeček, Milan Nádvorník, Vladimír Pejchal and Angelika Sebald
    119Sn and 13C NMR Spectral Study of Some Vinyltin(IV) Compounds Involving the Sn-S Bond
    1994, Vol. 59, Issue 4, pp. 885–897 [Abstract]
  • Josef Jirman
    1H and 13C NMR Spectra of Technically Important Sodium 1- and 2-Aminonaphthalenesulfonates
    1993, Vol. 58, Issue 6, pp. 1378–1387 [Abstract]
  • Dalimil Dvořák, David Šaman, Zdeněk Arnold, Ivana Císařová and Václav Petříček
    Cycloaddition Reactions of Arylmethylenemalonaldehydes with Olefins
    1992, Vol. 57, Issue 11, pp. 2337–2358 [Abstract]
  • Josef Jirman and Pavel Pech
    17O NMR Spectra of Acylated Ureas and Thioureas
    1992, Vol. 57, Issue 6, pp. 1278–1281 [Abstract]
  • Miloslav Hejsek, Jan Slouka, Vojtěch Bekárek and Antonín Lyčka
    Cyclization Reactions of 2-(6-Azauracil-5-yl)benzoic Acid and Some Its Derivatives
    1992, Vol. 57, Issue 1, pp. 123–133 [Abstract]
  • Josef Jirman
    1H and 13C NMR spectra of 2,2’-disubstitutedtrans-azobenzenes suitable for preparation of metallized azo dyes
    1991, Vol. 56, Issue 10, pp. 2160–2168 [Abstract]
  • Jaroslav Holeček, Antonín Lyčka, Milan Nádvorník and Karel Handlíř
    IR and 13C, 17O, and 119Sn NMR spectra of some bis(1-butyl)tin(IV) carboxylates of dicarboxylic acids
    1991, Vol. 56, Issue 9, pp. 1908–1915 [Abstract]
  • Antonín Lyčka and Karel Palát, Jr.
    A 15N, 13C, and 1H NMR study of reaction products from arylguanidines and chloroformate esters
    1991, Vol. 56, Issue 7, pp. 1505–1511 [Abstract]
  • Jiří Čermák, Miloslav Sebránek, Zora Nývltová and Josef Jirman
    Application of capillary GC-MS to analyses of wastes from chemical plants. Identification of N-arylphthalimides in naphthalenic pitches
    1991, Vol. 56, Issue 4, pp. 809–821 [Abstract]
  • Jiří Gasparič, Tomáš Vontor, Antonín Lyčka and Dobroslav Šnobl
    Formation of acetals and cleavage of the five-membered ring in the bromination of isatin in alcohols
    1990, Vol. 55, Issue 12, pp. 2963–2966 [Abstract]
  • Ladislav Lešetický, Stanislav Smrček, Vladimír Sváta, Jana Podlahová, Jaroslav Podlaha and Ivana Císařová
    The synthesis and X-ray structure of 3,7-diiododibenzosuberone. Synthesis of 3,7-diiodoamitriptyline
    1990, Vol. 55, Issue 11, pp. 2677–2684 [Abstract]
  • Karel Dlabal, Karel Palát, Antonín Lyčka and Želmíra Odlerová
    Synthesis and 1H and 13C NMR spectra of sulfur derivatives of pyrazine derived from amidation product of 2-chloropyrazine and 6-chloro-2-pyrazinecarbonitrile. Tuberculostatic activity
    1990, Vol. 55, Issue 10, pp. 2493–2501 [Abstract]
  • Jaroslav Holeček, Antonín Lyčka, Karel Handlíř and Milan Nádvorník
    13C and 119Sn NMR spectra of diphenyl- and dibenzyltin(IV) compounds and their complexes
    1990, Vol. 55, Issue 5, pp. 1193–1207 [Abstract]
  • Josef Jirman and Antonín Lyčka
    33S NMR spectra of some sulfonated naphthalenes, naphthols, and their anions
    1990, Vol. 55, Issue 2, pp. 446–451 [Abstract]
  • Antonín Lyčka, Miroslav Nečas, Josef Jirman, Jaroslav Straka and Bohdan Schneider
    NMR studies of 1-phenylazo-3-substituted-2-naphthols in solution and in the solid state
    1990, Vol. 55, Issue 1, pp. 193–201 [Abstract]
  • Josef Jirman, Antonín Lyčka and Miroslav Ludwig
    13C and 15N NMR spectra of oximes prepared by nitrosation of activated methylene group
    1990, Vol. 55, Issue 1, pp. 136–146 [Abstract]
  • Oldřich Pytela, Josef Jirman and Antonín Lyčka
    Chemometrical analysis of substituent effects on 13C and 15N NMR chemical shifts in 1-aroyl-3-substituted thioureas
    1989, Vol. 54, Issue 9, pp. 2399–2407 [Abstract]
  • Antonín Lyčka, Jaroslav Holeček and Karel Handlíř
    119Sn, 13C and 1H NMR studies of aryloxy- and arylthio(1-butyl)stannanes
    1989, Vol. 54, Issue 9, pp. 2386–2398 [Abstract]
  • Tomáš Vontor, Karel Palát and Antonín Lyčka
    Homolytic carbamoylation and alkoxycarbonylation of 2-aminopyrazine
    1989, Vol. 54, Issue 5, pp. 1306–1310 [Abstract]
  • Karel Komers, Antonín Lyčka, Josef Jirman and Ivan Kolb
    An intermediate of reaction of 2-naphthol with activated sludge
    1988, Vol. 53, Issue 7, pp. 1574–1578 [Abstract]
  • Vladimír Macháček, Vojeslav Štěrba, Ivan Kolb and Antonín Lyčka
    Reactions of methyl esters of N-(2,4-dinitrophenyl)glycine and N-methyl-N-(2,4-dinitrophenyl)glycine with sodium methoxide
    1988, Vol. 53, Issue 5, pp. 1044–1052 [Abstract]
  • Jaromír Kaválek, Vladimír Macháček, Vojeslav Štěrba and Antonín Lyčka
    Formation of N-methyl-2-nitroso-4,6-dinitroaniline from methyl ester of N-methyl-N-(2,4,6-trinitrophenyl)glycine
    1988, Vol. 53, Issue 5, pp. 1033–1043 [Abstract]
  • Jaromír Kaválek, Josef Jirman, Vladimír Macháček and Vojeslav Štěrba
    The methanolysis kinetics and dissociation constants of 1-(subst. benzoyl)-3-phenylthioureas
    1988, Vol. 53, Issue 3, pp. 593–600 [Abstract]
  • Antonín Lyčka, Josef Jirman and Jaroslav Holeček
    17O and 13C NMR spectra of some geminal diacetates
    1988, Vol. 53, Issue 3, pp. 588–592 [Abstract]
  • Jaroslav Holeček, Antonín Lyčka, Karel Handlíř and Milan Nádvorník
    13C and 119Sn NMR evidence of the presence and extent of σ-π conjugation in some benzyltin compounds and their complexes
    1988, Vol. 53, Issue 3, pp. 571–580 [Abstract]
  • Miloš Titz, Miloš Nepraš, Miroslav Nečas, Radim Hrdina, Stanislav Luňák, Jr. and Antonín Lyčka
    Study of the azo-hydrazone tautomeric equilibrium by electronic spectroscopy and quantum chemistry. II. HMO calculations
    1988, Vol. 53, Issue 2, pp. 227–242 [Abstract]
  • Miloš Nepraš, Miloš Titz, Miroslav Nečas, Stanislav Luňák, Jr., Radim Hrdina and Antonín Lyčka
    Study of the azo-hydrazone tautomeric equilibrium by electronic spectroscopy and quantum chemistry. I. Electronic spectra
    1988, Vol. 53, Issue 2, pp. 213–226 [Abstract]
  • Antonín Lyčka, Vladimír Macháček and Josef Jirman
    15N, 13C, and 1H NMR spectra of 1-substituted-2,4,6-trinitrobenzenes
    1987, Vol. 52, Issue 12, pp. 2946–2952 [Abstract]
  • Josef Jirman and Antonín Lyčka
    15N, 13C, and 1H NMR spectra of acylated ureas and thioureas
    1987, Vol. 52, Issue 10, pp. 2474–2481 [Abstract]
  • Jaromír Kaválek, Josef Jirman, Vladimír Macháček and Vojeslav Štěrba
    An anomalous effect of methyl group on acidity of acylthioureas
    1987, Vol. 52, Issue 8, pp. 1992–1998 [Abstract]
  • Jiří Brynda, Bohumil Kratochvíl and Ivana Císařová
    The determination of crystal structure of chromium(II) phosphite dihydrate, CrHPO3 2 H2O
    1987, Vol. 52, Issue 7, pp. 1742–1747 [Abstract]
  • Antonín Lyčka, Libuše Havlíčková, Alois Koloničný and Josef Jirman
    15N NMR study of amino-imino tautomerism in derivatives of 1,4-bis(substituted amino)-9,10-anthraquinones and 1,4-bis(substituted amino)-2,3-dihydro-9,10-anthraquinones
    1987, Vol. 52, Issue 3, pp. 736–741 [Abstract]
  • Antonín Lyčka, Tibor Liptaj and Josef Jirman
    13C and 15N NMR spectra of 3-methyl-1-phenylpyrazole-4,5-dione 4-(4'-substituted phenyl)hydrazones
    1987, Vol. 52, Issue 3, pp. 727–735 [Abstract]
  • Vladimír Macháček, Vojeslav Štěrba and Antonín Lyčka
    Mechanism of the reaction of 1-methoxy- and 1-chloro-2,4,6-trinitrobenzene with dimethyl malonate anion
    1987, Vol. 52, Issue 1, pp. 132–139 [Abstract]
  • Jaromír Kaválek, Josef Jirman and Vojeslav Štěrba
    Reactions of 1,3-diacylthioureas with methoxide ion and with amines
    1987, Vol. 52, Issue 1, pp. 120–131 [Abstract]
  • Antonín Lyčka, Jaroslav Holeček, Karel Handlíř, Josef Pola and Václav Chvalovský
    17O, 13C, and 29Si NMR spectra of some acyloxy- and diacetoxysilanes and acetoxygermanes
    1986, Vol. 51, Issue 11, pp. 2582–2589 [Abstract]
  • Jaroslav Holeček, Antonín Lyčka and Roland Wagener
    The 119Sn and 15N NMR spectral study of the chelate formation in the triphenyltin(IV) oxinate
    1986, Vol. 51, Issue 10, pp. 2116–2126 [Abstract]
  • Vladimír Macháček, Makky M. M. Hassanien, Vojeslav Štěrba and Antonín Lyčka
    Formation of the Meisenheimer spiro adduct of N-(2,4,6-trinitrophenyl)alanine methylamide and its rearrangement to 2-amino-N-methyl-N-(2,4,6-trinitrophenyl)propanamide
    1986, Vol. 51, Issue 9, pp. 1972–1985 [Abstract]
  • Jaroslav Holeček, Karel Handlíř, Antonín Lyčka, T. K. Chattopadhyay, B. Majee and A. K. Kumar
    Preparation and infrared and 13C, 17O, and 119Sn NMR spectra of some substituted di- and tri(1-butyl)tin phenoxyacetates and phenylthioacetates
    1986, Vol. 51, Issue 5, pp. 1100–1111 [Abstract]
  • Vladimír Macháček, Antonín Lyčka and Milan Nádvorník
    A study of reaction of aromatic polynitro compounds with tributylstannyl hydride
    1985, Vol. 50, Issue 11, pp. 2598–2606 [Abstract]
  • Dobroslav Šnobl, Antonín Lyčka and Jaroslav Horyna
    13C NMR spectra of sodium naphthalenesulphonates
    1985, Vol. 50, Issue 8, pp. 1852–1861 [Abstract]
  • Jaromír Kaválek, Josef Jirman and Vojeslav Štěrba
    Kinetics and mechanism of rearrangement and methanolysis of acylphenylthioureas
    1985, Vol. 50, Issue 3, pp. 766–778 [Abstract]
  • Antonín Lyčka, Milan Nádvorník, Karel Handlíř and Jaroslav Holeček
    13C and 119Sn NMR spectra of some triphenyltin 4-substituted benzoates dissolved in coordinating and non-coordinating solvents
    1984, Vol. 49, Issue 12, pp. 2903–2911 [Abstract]
  • Antonín Lyčka
    13C, 15N, and 19F NMR spectra of 2-phenylhydrazonopropanedinitriles and methyl 2-phenyl hydrazonocyanoacetates
    1984, Vol. 49, Issue 12, pp. 2801–2806 [Abstract]
  • Jan Slouka, Vojtěch Bekárek, Karel Nálepa and Antonín Lyčka
    Synthesis of 1,2,4-triazino[5,6-b]- and imidazo[4,5-b]quinoline derivatives
    1984, Vol. 49, Issue 11, pp. 2628–2634 [Abstract]
  • Karel Handlíř, Jaroslav Holeček, Milan Nádvorník, Antonín Lyčka and Milan Hucl
    Study of structure of bis(triphenylstannyl) chromate(VI) by infrared, Mössbauer, and 1H, 13C and 119Sn NMR spectra
    1984, Vol. 49, Issue 6, pp. 1497–1504 [Abstract]
  • Antonín Lyčka and Pavel Vetešník
    13C and 15N NMR spectra of 1-(3- or 4-substituted phenyl)-3-methyl-3-phenyltriazenes
    1984, Vol. 49, Issue 4, pp. 963–969 [Abstract]
  • Vladimír Macháček and Antonín Lyčka
    13C and 15N NMR spectra of 6-substituted bicyclo[3,3,1]7-nonanone nitronates
    1984, Vol. 49, Issue 1, pp. 244–252 [Abstract]
  • Antonín Lyčka and Jaromír Kaválek
    13C, 15N, and 19F NMR spectra of 4-fluoro-(3´ or 4´-substituted) azobenzenes
    1984, Vol. 49, Issue 1, pp. 58–64 [Abstract]
  • Antonín Lyčka
    13C and 15N NMR study of azo-hydrazone tautomerism in azo dyes containing amino or acetamido groups
    1983, Vol. 48, Issue 11, pp. 3104–3111 [Abstract]
  • Jan Slouka, Vojtěch Bekárek and Antonín Lyčka
    Cyclization reactions of some o-acylphenylhydrazones
    1982, Vol. 47, Issue 6, pp. 1746–1756 [Abstract]
  • Bohumír Koutek, Milena Píšová, Josef Krupička, Antonín Lyčka, Dobroslav Šnobl and Milan Souček
    Benzoannelated quinone methides
    1982, Vol. 47, Issue 6, pp. 1645–1653 [Abstract]
  • Antonín Lyčka
    Carbon-13 and nitrogen-15 NMR spectra of cis- and trans-azobenzene, 4-monosubstituted and 4,4'-disubstituted trans-azobenzenes
    1982, Vol. 47, Issue 4, pp. 1112–1120 [Abstract]
  • Antonín Lyčka, Dobroslav Šnobl, Karel Handlíř, Jaroslav Holeček and Milan Nádvorník
    29Si and 13C NMR spectra of some alkyldiphenylchlorosilanes, alkyldiphenylsilanoles and bis(alkyldiphenylsilyl)chromates
    1982, Vol. 47, Issue 2, pp. 603–612 [Abstract]
  • Bohumír Koutek, Lubomír Musil, Jiří Velek, Antonín Lyčka, Dobroslav Šnobl, Miroslava Synáčková and Milan Souček
    Perturbation of the fuchsone chromophore by 3,5-methyl substitution. Sterically crowded exocyclic double bond
    1981, Vol. 46, Issue 10, pp. 2540–2556 [Abstract]
  • Antonín Lyčka, Dobroslav Šnobl, Bohumír Koutek, Libuše Pavlíčková and Milan Souček
    13C NMR study of 7,7-disubstituted quinone methides
    1981, Vol. 46, Issue 9, pp. 2083–2090 [Abstract]
  • Antonín Lyčka, Dobroslav Šnobl, Bohumír Koutek, Libuše Pavlíčková and Milan Souček
    13C NMR study of substituted quinone methides. 2- and 2,6-substituted fuchsones
    1981, Vol. 46, Issue 8, pp. 1775–1787 [Abstract]
  • Antonín Lyčka, Dobroslav Šnobl, Karel Handlíř, Jaroslav Holeček and Milan Nádvorník
    13C, 29Si, 115Sn, 117Sn and 119Sn NMR spectra of some triphenyl derivatives of elements of IVB group
    1981, Vol. 46, Issue 6, pp. 1383–1388 [Abstract]
  • Antonín Lyčka and Dobroslav Šnobl
    Coupling constants nitrogen-15-nitrogen-15 and nitrogen-15-hydrogen in phenylhydrazones forming hydrogen bond
    1981, Vol. 46, Issue 4, pp. 892–897 [Abstract]
  • Antonín Lyčka
    13C and 15N NMR studies of 2,3,4-pentanetrione 3-phenylhydrazone, dimethyl 2-phenylhydrazonopropanedioate and ethyl 2-phenylhydrazono-3-oxobutanoate
    1980, Vol. 45, Issue 12, pp. 3354–3359 [Abstract]
  • Antonín Lyčka
    Carbon-13 and nitrogen-14 NMR spectra of 1-(substituted phenyl)pyridinium salts
    1980, Vol. 45, Issue 10, pp. 2766–2771 [Abstract]
  • Jaroslav Horyna, Antonín Lyčka and Dobroslav Šnobl
    13C-NMR spectra of benzenesulphonyl derivatives
    1980, Vol. 45, Issue 5, pp. 1575–1580 [Abstract]
  • Antonín Lyčka and Dobroslav Šnobl
    Effect of lanthanide shift reagents on 1H NMR spectra of aminopyridines
    1979, Vol. 44, Issue 3, pp. 908–911 [Abstract]