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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 35, 2005 - Issue 3

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Diastereoselective Synthesis of Anti‐β‐Substituted α‐Aminobutanoic Acids via Michael Addition Reactions of Nucleophiles to New Chiral Ni(II) Complexes of Dehydroaminobutanoic Acid

A. S. Saghiyan Yerevan State University, Chemistry Department, Faculty of Pharmaceutical Chemistry, 1 Manukyan, 375025, Yerevan, Republic of ArmeniaCorrespondence[email protected]

H. H. Hambardzumyan Yerevan State University, Chemistry Department, Faculty of Pharmaceutical Chemistry, 1 Manukyan, 375025, Yerevan, Republic of Armenia

L. L. Manasyan Yerevan State University, Chemistry Department, Faculty of Pharmaceutical Chemistry, 1 Manukyan, 375025, Yerevan, Republic of Armenia

A. A. Petrosyan Yerevan State University, Chemistry Department, Faculty of Pharmaceutical Chemistry, 1 Manukyan, 375025, Yerevan, Republic of Armenia

V. I. Maleev A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

A. S. Peregudov A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia

Pages 449-459 | Received 20 Oct 2004, Published online: 28 Jul 2007

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https://doi.org/10.1081/SCC-200048957

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Yoshinori Tokairin, Yuhei Shigeno, Jianlin Han, Gerd‐Volker Röschenthaler, Hiroyuki Konno, Hiroki Moriwaki & Vadim A. Soloshonok. (2020) Asymmetric Synthesis of 4,4‐(Difluoro)glutamic Acid via Chiral Ni(II)‐Complexes of Dehydroalanine Schiff Bases. Effect of the Chiral Ligands Structure on the Stereochemical Outcome. ChemistryOpen 9:1, pages 93-96.
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Wenzhong Zhang, Romuald Eto Ekomo, Christian Roussel, Hiroki Moriwaki, Hidenori Abe, Jianlin Han & Vadim A. Soloshonok. (2018) Axially chiral Ni(II) complexes of α-amino acids: Separation of enantiomers and kinetics of racemization. Chirality 30:4, pages 498-508.
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Ryosuke Takeda, Hidenori Abe, Norio Shibata, Hiroki Moriwaki, Kunisuke Izawa & Vadim A. Soloshonok. (2017) Asymmetric synthesis of α-deuterated α-amino acids. Organic & Biomolecular Chemistry 15:33, pages 6978-6983.
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Yong Nian, Jiang Wang, Hiroki Moriwaki, Vadim A. Soloshonok & Hong Liu. (2017) Analysis of crystallographic structures of Ni( ii ) complexes of α-amino acid Schiff bases: elucidation of the substituent effect on stereochemical preferences . Dalton Transactions 46:13, pages 4191-4198.
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Ashot S. Saghyan & Peter Langer. 2016. Asymmetric Synthesis of Non&;#x02010;Proteinogenic Amino Acids. Asymmetric Synthesis of Non&;#x02010;Proteinogenic Amino Acids 159 352 .

José Luis Aceña, Alexander E. Sorochinsky & Vadim Soloshonok. (2014) Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations. Amino Acids 46:9, pages 2047-2073.
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Ashot S. Saghyan, Hayarpi M. Simonyan, Lala A. Stepanyan, Samvel G. Ghazaryan, Arpine V. Geolchanyan, Luiza L. Manasyan, Vahe T. Ghochikyan, Tariel V. Ghochikyan, Nelli A. Hovhannisyan, Ashot Gevorgyan, Viktor O. Iaroshenko & Peter Langer. (2012) Asymmetric synthesis of new β-heterocyclic (S)-α-aminopropionic acids. Tetrahedron: Asymmetry 23:11-12, pages 891-897.
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Alexander Popkov & Bart De Spiegeleer. (2012) Chiral nickel( ii ) complexes in the preparation of 11 C- and 18 F-labelled enantiomerically pure α-amino acids . Dalton Trans. 41:5, pages 1430-1440.
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Ashot S. Saghyan, Ani S. Dadayan, Slavik A. Dadayan, Anna F. Mkrtchyan, Arpine V. Geolchanyan, Luiza L. Manasyan, Hrant R. Ajvazyan, Victor N. Khrustalev, Hasmik H. Hambardzumyan & Victor I. Maleev. (2010) Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries. Tetrahedron: Asymmetry 21:24, pages 2956-2965.
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Alexander Popkov & Martin Breza. (2010) Why is monoalkylation versus bis-alkylation of the Ni(II) complex of the Schiff base of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and glycine so selective? MP2 modelling and topological QTAIM analysis of chiral metallocomplex synthons of α-amino acids used for the preparation of radiopharmaceuticals for positron emission tomography. Journal of Radioanalytical and Nuclear Chemistry 286:3, pages 829-833.
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Alexander Popkov, Jiří Hanusek, Jiří Čermák, Vratislav Langer, Robert Jirásko, Michal Holčapek & Milan Nádvorník. (2010) Development of metallocomplex amino acids synthons for the asymmetric preparation of α-amino acids by stereoselective introduction of a side chain. Evaluation of the model asymmetric preparation of alanine and β-13C monolabelled α-aminoisobutyric acid. Journal of Radioanalytical and Nuclear Chemistry 285:3, pages 621-626.
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V. O. Topuzyan, M. M. Kazandzhyan, R. A. Tamazyan & A. G. Aivazyan. (2009) Derivatives of α,β-dehydroamino acids: V. Intramolecular cyclization of 2-{2-[(Z)-1-Benzamido-2-phenylvinyl]acetamidomethyl}benzimidazole. Russian Journal of Organic Chemistry 45:2, pages 215-217.
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Milan Nádvorník, Vratislav Langer, Robert Jirásko, Michal Holčapek, Tomáš Weidlich, Antonín Lyčka & Alexander Popkov. (2008) Syntheses, X-ray, MS , NMR and CD structure determination of nickel(II) complexes of Schiff bases of (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide and aromatic α-amino acids. Polyhedron 27:17, pages 3477-3483.
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Alexander Popkov, Milan Nádvorník, Pavla Kružberská, Antonín Lyčka, Szabolcs Lehel & Nicholas Gillings. (2007) Towards stereoselective radiosynthesis of α-[11C]methyl-substituted aromatic α-amino acids – a challenge of creation of quaternary asymmetric centre in a very short time. Journal of Labelled Compounds and Radiopharmaceuticals 50:5-6, pages 370-374.
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Vratislav Langer, Alexander Popkov, Milan N?dvorn?k & Anton?n Ly?ka. (2007) Two new Ni(II) Schiff base complexes: X-ray absolute structure determination, synthesis of a 15N-labelled complex and full assignment of its 1H NMR and 13C NMR spectra. Polyhedron 26:4, pages 911-917.
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Ashot S. Saghiyan, Luisa L. Manasyan, Arpine V. Geolchanyan, Anahit M. Hovhannisyan, Tariel V. Ghochikyan, Vilik S. Haroutunyan, Aida A. Avetisyan, Koryun S. Mirzoyan, Victor I. Maleev & Victor N. Khrustalev. (2006) Asymmetric synthesis of anti-diastereoisomers of β-heterocycle substituted (S)-α-aminobutyric acids. Tetrahedron: Asymmetry 17:19, pages 2743-2753.
Crossref

A. S. Saghiyan, L. L. Manasyan, S. A. Dadayan, S. G. Petrosyan, A. A. Petrosyan, V. I. Maleev & V. N. Khrustalev. (2006) Novel modified chiral NiII complexes with the Schiff bases of (E)-and (Z)-2-aminobut-2-enoic acids: Synthesis and study. Russian Chemical Bulletin 55:3, pages 442-450.
Crossref

A. S. Saghiyan, H. H. Hambardzumyan, L. L. Manasyan, A. A. Petrosyan, V. I. Maleev & A. S. Peregudov. (2005) Diastereoselective Synthesis of anti‐β‐Substituted α‐Aminobutanoic Acids via Michael Addition Reactions of Nucleophiles to New Chiral Ni(II) Complexes of Dehydroaminobutanoic Acid.. ChemInform 36:30.
Crossref

Alexander Popkov, Ivana Císařová, Jana Sopková, Josef Jirman, Antonín Lyčka & Konstantin A. Kochetkov. (2005) 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. Collection of Czechoslovak Chemical Communications 70:9, pages 1397-1410.
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Diastereoselective Synthesis of Anti‐β‐Substituted α‐Aminobutanoic Acids via Michael Addition Reactions of Nucleophiles to New Chiral Ni(II) Complexes of Dehydroaminobutanoic Acid

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Diastereoselective Synthesis of Anti‐β‐Substituted α‐Aminobutanoic Acids via Michael Addition Reactions of Nucleophiles to New Chiral Ni(II) Complexes of Dehydroaminobutanoic Acid

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