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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 4
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Original Articles

Catalytic stereoselective synthesis of α-Amino phosphonic acid derivatives by asymmetric hydrogenation

Ute Schmidt Institut für Organische Katalyseforschung an der Universität Rostock e.V, Buchbinderstr. 5-6, D-18055, Rostock, Germany
,
Günther Oehme Institut für Organische Katalyseforschung an der Universität Rostock e.V, Buchbinderstr. 5-6, D-18055, Rostock, Germany
&
Hanswalter Krause Institut für Organische Katalyseforschung an der Universität Rostock e.V, Buchbinderstr. 5-6, D-18055, Rostock, Germany
Pages 777-781 | Received 24 Jul 1995, Published online: 21 Nov 2007

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Oleg I. Kolodiazhnyi. (2014) Advances in Asymmetric Hydrogenation and Hydride Reduction of Organophosphorus Compounds. Phosphorus, Sulfur, and Silicon and the Related Elements 189:7-8, pages 1102-1131.
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Dae Young Kim, Ki Hyung Suh, Sun Chul Huh & Kilsung Lee. (2001) MICHAEL ADDITION OF N-(DIPHENYLMETHYLENE)- AMINOMETHYLPHOSPHONATE TO ACRYLATES USING PHASE TRANSFER CATALYSIS CONDITIONS: SYNTHESIS OF 1-(N-DIPHENYLMETHYLENE)AMINO- 3-(ALKOXYCARBONYL)- PROPYLPHOSPHONATES. Synthetic Communications 31:21, pages 3315-3322.
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Torsten Dwars, Ute Schmidt, Christine Fischer, Ingrid Grassert, Hans-Walter Krause, Manfred Michalik & Günther Oehme. (2000) SYNTHESIS OF ENANTIOMERICALLY ENRICHED α-AMINOPHOSPHINIC ACID DERIVATIVES VIA ASYMMETRIC HYDROGENATION. Phosphorus, Sulfur, and Silicon and the Related Elements 158:1, pages 209-240.
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Articles from other publishers (40)

Hong-Quan Du. (2022) Rh-catalyzed asymmetric hydrogenation of α- and β-enamido phosphonates: highly enantioselective access to amino phosphonic acids. Organic & Biomolecular Chemistry 20:45, pages 8843-8848.
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Barry M. Trost, Anand H. Shinde, Youliang Wang, Zhijun Zuo & Chang Min. (2020) Palladium-Catalyzed Regio-, Enantio-, and Diastereoselective Asymmetric [3 + 2] Cycloaddition Reactions: Synthesis of Chiral Cyclopentyl Phosphonates. ACS Catalysis 10:3, pages 1969-1975.
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Pauline Adler, Antoine Fadel, Joëlle Prunet & Nicolas Rabasso. (2017) From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis. Organic & Biomolecular Chemistry 15:2, pages 387-395.
Crossref
Oleg I. Kolodiazhnyi. 2016. Asymmetric Synthesis in Organophosphorus Chemistry. Asymmetric Synthesis in Organophosphorus Chemistry 187 252 .
Pauline Adler, Antoine Fadel & Nicolas Rabasso. (2014) Strategies for the synthesis of α- and β-amino vinylphosphonate. Tetrahedron 70:30, pages 4437-4456.
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Oleg I. Kolodiazhnyi, Valery P. Kukhar & Anastasy O. Kolodiazhna. (2014) Asymmetric catalysis as a method for the synthesis of chiral organophosphorus compounds. Tetrahedron: Asymmetry 25:12, pages 865-922.
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Pauline Adler, Filipe Gomes, Antoine Fadel & Nicolas Rabasso. (2013) Selective Reduction of Amino Allenephosphonates: Preparation of α-Amino Vinylphosphonates. European Journal of Organic Chemistry 2013:33, pages 7546-7555.
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Nicolas Lefevre, Jean-Louis Brayer, Benoît Folléas & Sylvain Darses. (2013) Chiral α-Amino Phosphonates via Rhodium-Catalyzed Asymmetric 1,4-Addition Reactions. Organic Letters 15:16, pages 4274-4276.
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Zheng-Chao Duan, Xiang-Ping Hu, Cheng Zhang & Zhuo Zheng. (2010) Enantioselective Rh-Catalyzed Hydrogenation of 3-Aryl-4-phosphonobutenoates with a P -Stereogenic BoPhoz-Type Ligand . The Journal of Organic Chemistry 75:23, pages 8319-8321.
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Zheng-Chao Duan, Xiang-Ping Hu, Cheng Zhang, Dao-Yong Wang, Sai-Bo Yu & Zhuo Zheng. (2009) Highly Enantioselective Rh-Catalyzed Hydrogenation of β,γ-Unsaturated Phosphonates with Chiral Ferrocene-Based Monophosphoramidite Ligands. The Journal of Organic Chemistry 74:23, pages 9191-9194.
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Mario Ordóñez, Haydée Rojas-Cabrera & Carlos Cativiela. (2009) An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives. Tetrahedron 65:1, pages 17-49.
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Min Qiu, Xiang-Ping Hu, Jia-Di Huang, Dao-Yong Wang, Jun Deng, Sai-Bo Yu, Zheng-Chao Duan & Zhuo Zheng. (2008) Modular Phosphine-Aminophosphine Ligands Based on Chiral 1,2,3,4-Tetrahydro-1-naphthylamine Backbone: A New Class of Practical Ligands for Enantioselective Hydrogenations. Advanced Synthesis & Catalysis 350:17, pages 2683-2689.
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Zheng‐Chao Duan, Xiang‐Ping Hu, Dao‐Yong Wang, Jia‐Di Huang, Sai‐Bo Yu, Jun Deng & Zhuo Zheng. (2008) Enantioselective Synthesis of Optically Active Alkanephos‐ phonates via Rhodium‐Catalyzed Asymmetric Hydrogenation of β‐Substituted α,β‐Unsaturated Phosphonates with Ferrocene‐Based Monophosphoramidite Ligands . Advanced Synthesis & Catalysis 350:13, pages 1979-1983.
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Joshua P. Abell & Hisashi Yamamoto. (2008) Catalytic Enantioselective Pudovik Reaction of Aldehydes and Aldimines with Tethered Bis(8-quinolinato) (TBOx) Aluminum Complex. Journal of the American Chemical Society 130:32, pages 10521-10523.
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Min Qiu, Xiang‐Ping Hu, Dao‐Yong Wang, Jun Deng, Jia‐Di Huang, Sai‐Bo Yu, Zheng‐Chao Duan & Zhuo Zheng. (2008) Chiral 1,2,3,4‐Tetrahydro‐1‐naphthylamine‐Derived Phosphine‐Phosphoramidite Ligand (THNAPhos): Application in Highly Enantioselective Hydrogenations of Functionalized CC Bonds. Advanced Synthesis & Catalysis 350:9, pages 1413-1418.
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Pedro Merino, Eugenia Marqués‐López & Raquel P. Herrera. (2008) Catalytic Enantioselective Hydrophosphonylation of Aldehydes and Imines. Advanced Synthesis & Catalysis 350:9, pages 1195-1208.
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Dao-Yong Wang, Jia-Di Huang, Xiang-Ping Hu, Jun Deng, Sai-Bo Yu, Zheng-Chao Duan & Zhuo Zheng. (2008) Readily Available Chiral Phosphine−Aminophosphine Ligands for Highly Efficient Rh-Catalyzed Asymmetric Hydrogenation of α-Enol Ester Phosphonates and α-Enamido Phosphonates. The Journal of Organic Chemistry 73:5, pages 2011-2014.
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Pallavi A. Badkar, Nigam P. Rath & Christopher D. Spilling. (2007) Asymmetric Synthesis of 2-Alkyl-3-phosphonopropanoic Acids via P−C Bond Formation and Hydrogenation. Organic Letters 9:18, pages 3619-3622.
Crossref
Jun-An Ma. (2006) Catalytic asymmetric synthesis of α- and β-amino phosphonic acid derivatives. Chem. Soc. Rev. 35:7, pages 630-636.
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E. V. Bayandina, E. Yu. Davydova, M. A. Abaskalova, R. Z. Musin & V. A. Al'fonsov. (2005) New reaction pathway of dialkyl phosphorochloridites with salts of α-benzylideneaminocarboxylic acids. Direct synthesis of α-aminophosphonates from isostructural α-benzylideneaminocarboxylic acids. Russian Chemical Bulletin 54:6, pages 1492-1495.
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G.L. Patrick. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 877 956 .
L. Micouin. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 79 119 .
Nikolaus Risch, Stefan Piper, Andreas Winter & Annette Lefarth-Risse. (2005) An Efficient Synthesis of Novel ?-Aminophosphonates Based on a Mannich-Type Reaction. European Journal of Organic Chemistry 2005:2, pages 387-394.
Crossref
Katarzyna Błażewska & Tadeusz Gajda. (2004) A concise synthesis of diethyl 1-(tert-butoxycarbonylamino)-1-alkenylphosphonates. Tetrahedron 60:51, pages 11701-11707.
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Ilya D. Gridnev, Masaya Yasutake, Tsuneo Imamoto & Irina P. Beletskaya. (2004) Asymmetric hydrogenation of α,β-unsaturated phosphonates with Rh-BisP* and Rh-MiniPHOS catalysts: Scope and mechanism of the reaction. Proceedings of the National Academy of Sciences 101:15, pages 5385-5390.
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Guy D. Joly & Eric N. Jacobsen. (2004) Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids. Journal of the American Chemical Society 126:13, pages 4102-4103.
Crossref
Joel D. Moore, Kevin T. Sprott & Paul R. Hanson. (2002) Conformationally Constrained α-Boc-Aminophosphonates via Transition Metal-Catalyzed/Curtius Rearrangement Strategies. The Journal of Organic Chemistry 67:23, pages 8123-8129.
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Akbar Heydari. (2002) Organic synthesis in an unconventional solvent, 5.0M lithium perchlorate/diethyl ether. Tetrahedron 58:34, pages 6777-6793.
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Béatrice Quiclet-Sire, Samir Z Zard & Haiwen Zhang. (2002) A practical access to α-phosphonoenamides. Journal of Organometallic Chemistry 643-644, pages 404-408.
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Allen A. Thomas & K. Barry Sharpless. (1999) The Catalytic Asymmetric Aminohydroxylation of Unsaturated Phosphonates. The Journal of Organic Chemistry 64:22, pages 8379-8385.
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Mark J. Burk, Timothy A. Stammers & Judith A. Straub. (1999) Enantioselective Synthesis of α-Hydroxy and α-Amino Phosphonates via Catalytic Asymmetric Hydrogenation. Organic Letters 1:3, pages 387-390.
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C Fischer, U Schmidt, T Dwars & G Oehme. (1999) Enantiomeric resolution of derivatives of α-aminophosphonic and α-aminophosphinic acids by high-performance liquid chromatography and capillary electrophoresis. Journal of Chromatography A 845:1-2, pages 273-283.
Crossref
Ingrid Grassert, Ute Schmidt, Silke Ziegler, Christine Fischer & Günther Oehme**. (1998) Use of rhodium complexes with amphiphilic and nonamphiphilic ligands for the preparation of chiral α-aminophosphonic acid esters by hydrogenation in micellar media. Tetrahedron: Asymmetry 9:23, pages 4193-4202.
Crossref
Torsten Dwars, Ute Schmidt, Christine Fischer, Ingrid Grassert, Rhett Kempe, Roland Fröhlich, Karlheinz Drauz & Günther Oehme. (1998) Herstellung optisch aktiver α-Aminophosphinsäuren durch asymmetrische katalytische Hydrierung in organischen Lösungsmitteln und wäßrig-micellarem Medium. Angewandte Chemie 110:20, pages 3033-3035.
Crossref
Jens Holz, Michael Quirmbach, Ute Schmidt, Detlef Heller, Rainer Stürmer & Armin Börner. (1998) Synthesis of a New Class of Functionalized Chiral Bisphospholane Ligands and the Application in Enantioselective Hydrogenations. The Journal of Organic Chemistry 63:22, pages 8031-8034.
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Akbar Heydari, Ali Karimian & Junes Ipaktschi. (1998) Lithium perchlorate/diethylether catalyzed aminophosphonation of aldehydes. Tetrahedron Letters 39:37, pages 6729-6732.
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Ute Schmidt, Hans Walter Krause, G�nther Oehme, Manfred Michalik & Christine Fischer. (1998) Enantioselective synthesis of ?-aminophosphonic acid derivatives by hydrogenation. Chirality 10:7, pages 564-572.
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Dae Young Kim & Dae Yong Rhie. (1997) Synthesis of α-aminoalkylphosphonates from vinylphosphonates via aziridinylphosphonates. Tetrahedron 53:40, pages 13603-13608.
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Thomas Wirth, Walter Leitner, Axel Trautwein, Marcus Bauser, Jörg Früchtel, Hartmut Richter, Günther Jung, Michael Schultz & Christos Tsaklakidis. (1997) Organische Chemie 1996. Nachrichten aus Chemie, Technik und Laboratorium 45:2, pages 148-165.
Crossref
U. SCHMIDT, G. OEHME & H. KRAUSE. (2010) ChemInform Abstract: Catalytic Stereoselective Synthesis of α‐Amino Phosphonic Acid Derivatives by Asymmetric Hydrogenation.. ChemInform 27:25.
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