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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 1
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Original Articles

Asymmetric Synthesis of Diethyl α-Amino-α-Alkyl-Phosphonates by Alkylation of the Chiral Schiff Base Derived from (+)-Ketopinic Acid and Diethylaminomethyl Phosphonate

M. Ferrari Dipartimento di Chimica, Organica e Industriale Università, degli Studi di Milano Via Venezian, 21, 20133, Milano, Italy
,
G. Jommi Dipartimento di Chimica, Organica e Industriale Università, degli Studi di Milano Via Venezian, 21, 20133, Milano, Italy
,
G. Miglierini Dipartimento di Chimica, Organica e Industriale Università, degli Studi di Milano Via Venezian, 21, 20133, Milano, Italy
,
R. Pagliarin Dipartimento di Chimica, Organica e Industriale Università, degli Studi di Milano Via Venezian, 21, 20133, Milano, Italy
&
M. Sisti Dipartimento di Chimica, Organica e Industriale Università, degli Studi di Milano Via Venezian, 21, 20133, Milano, Italy
Pages 107-123 | Received 08 Jul 1991, Published online: 23 Sep 2006

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V.P. Kukhar'V.A. Soloshonok & V.A. Solodenko. (1994) Asymmetric Synthesis of Phosphorus Analogs of Amino Acids. Phosphorus, Sulfur, and Silicon and the Related Elements 92:1-4, pages 239-264.
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Articles from other publishers (26)

Oscar Abelardo Ramírez-Marroquín, Iván Romero-Estudillo, José Luis Viveros-Ceballos, Carlos Cativiela & Mario Ordóñez. (2016) Convenient Synthesis of Cyclic α-Aminophosphonates by Alkylation-Cyclization Reaction of Iminophosphoglycinates Using Phase-Transfer Catalysis. European Journal of Organic Chemistry 2016:2, pages 308-313.
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Gregory Roos. 2014. Key Chiral Auxiliary Applications. Key Chiral Auxiliary Applications 263 325 .
Anil D. Naik, Joséphine Beck, Marinela M. Dîrtu, Carine Bebrone, Bernard Tinant, Koen Robeyns, Jacqueline Marchand-Brynaert & Yann Garcia. (2011) Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and β-lactamase assay. Inorganica Chimica Acta 368:1, pages 21-28.
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R. S. Edmundson. 2009. PATAI'S Chemistry of Functional Groups. PATAI'S Chemistry of Functional Groups.
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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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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Amos B. SmithIIIIII, Kraig M. Yager, Barton W. Phillips & Carol M. Taylor. 2003. Organic Syntheses. Organic Syntheses 19 19 .
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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Silvio AimeMauro BottaLuca FrullanoSimonetta Geninatti CrichGiovanni GiovenzanaRoberto PagliarinGiovanni PalmisanoFederico Riccardi SirtoriMassimo Sisti. (2000) [GdPCP2A(H 2 O) 2 ] - : A Paramagnetic Contrast Agent Designed for Improved Applications in Magnetic Resonance Imaging . Journal of Medicinal Chemistry 43:21, pages 4017-4024.
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Jingbo Xiao, Xiaomei Zhang & Chengye Yuan. (2000) A facile asymmetric synthesis of 1-amino-2,2,2-trifluoroethanephosphonic acid. Heteroatom Chemistry 11:7, pages 536-540.
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Jiaxi Xu, Yuan Ma & Lifang Duan. (2000) A novel synthetic route to N-protected 1-aminoalkylphosphonates. Heteroatom Chemistry 11:6, pages 417-421.
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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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Masakatsu Shibasaki, Hiroaki Sasai & Takayoshi Arai. (2003) Asymmetric Catalysis with Heterobimetallic Compounds. Angewandte Chemie International Edition in English 36:12, pages 1236-1256.
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Masakatsu Shibasaki, Hiroaki Sasai & Takayoshi Arai. (1997) Asymmetrische Katalyse mit Hetero-Dimetall-Verbindungen. Angewandte Chemie 109:12, pages 1290-1311.
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Artur Ryglowski & Pawel Kafarski. (1996) Preparation of 1-aminoalkylphosphonic acids and 2-aminoalkylphosphonic acids by reductive amination of oxoalkylphosphonates. Tetrahedron 52:32, pages 10685-10692.
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Thomas Oberhauser & Vladimir Meduna. (1996) On the stereochemical purity of (+)-7-aminocephalosporanic acid. Tetrahedron 52:22, pages 7691-7702.
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I Craig Baldwin, Jonathan MJ Williams & R Paul Beckett. (1995) α-Aminophosphonate derivatives as nucleophiles in diastereoselective and enantioselective palladium catalysed allylic substitution reactions. Tetrahedron: Asymmetry 6:3, pages 679-682.
Crossref
Giulia Cabella, Giancarlo Jommi, Roberto Pagliarin, Guido Sello & Massimo Sisti. (1995) Alkylation of chiral phosphonoglycine equivalents: Asymmetric synthesis of diethyl α-amino-α-alkyl-phosphonates. Tetrahedron 51:6, pages 1817-1826.
Crossref
. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1085 1229 .
Frances Heaney. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 451 504 .
Martin J. O'Donnell, Linda K. Lawley, Pradeep B. Pushpavanam, Alain Burger, F.G. Bordwell & Xian-Man Zhang. (1994) Preparation of an α-aminophosphonate cation equivalent and its reaction with organoboranes. Tetrahedron Letters 35:35, pages 6421-6424.
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Valerii P Kukhar'N Yu Svistunova, V A Solodenko & Vadim A Soloshonok. (1993) Asymmetric synthesis of fluorine- and phosphorus-containing analogues of aminoacids. Russian Chemical Reviews 62:3, pages 261-278.
Crossref
Catherine Maury, Jacques Royer & Henri-Philippe Husson. (1992) A simple and general method for the asymmetric synthesis of α-aminophosphonic acids. Tetrahedron Letters 33:41, pages 6127-6130.
Crossref
Giancarlo Jommi, Giuliana Miglierini, Roberto Pagliarin, Guido Sello & Massimo Sisti. (1992) Asymmetric synthesis of diethyl α-amino- α-alkyl-phosphonates by alkylation of chiral phosphonoglycine equivalents: Role of chelating effects. Tetrahedron: Asymmetry 3:9, pages 1131-1134.
Crossref
M. FERRARI, G. JOMMI, G. MIGLIERINI, R. PAGLIARIN & M. SISTI. (2010) ChemInform Abstract: Asymmetric Synthesis of Diethyl α‐Amino‐α‐ alkylphosphonates by Alkylation of the Chiral Schiff Base Derived from (+)‐Ketopinic Acid and Diethylaminomethyl Phosphonate.. ChemInform 23:23.
Crossref
Giancarlo Jommi, Giuliana Miglierini, Roberto Pagliarin, Giudo Sello & Massimo Sisti. (1992) Studies toward a model for predicting the diastereoselectivity in the electrophilic amination of chiral 1,3,2-oxazaphospholanes. Tetrahedron 48:35, pages 7275-7288.
Crossref

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