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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 3
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Original Articles

An Asymmetric Strecker Synthesis of (R)-(+)-2-Methyl-3-Phenylalanine: An Efficient Preparation

Pullachipatti K. Subramanian Department of Medicinal Chemistry College of Pharmacy, University of Michigan, Ann Arbor, Mi, 48109-1065
&
Ronald W. Woodard Department of Medicinal Chemistry College of Pharmacy, University of Michigan, Ann Arbor, Mi, 48109-1065
Pages 337-342 | Published online: 19 Dec 2006

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Yoshiyasu ICHIKAWA, Eiji YAMAUCHI & Minoru ISOBE. (2005) Allyl Cyanate-to-isocyanate Rearrangement for the Synthesis of Quaternary Stereocenter with Nitrogen Substituent. Bioscience, Biotechnology, and Biochemistry 69:5, pages 939-943.
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Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Louis Fieser & Janice Smith. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
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Thomas Wirth. 2003. Organic Synthesis Set. Organic Synthesis Set 26 33 .
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Irina Iovel, Lena Golomba, Juris Popelis & Edmunds Lukevics. (2002) Diastereoselective addition of trimethylsilyl cyanide to chiral O ‐, S ‐ and N ‐heterocyclic aldimines . Applied Organometallic Chemistry 16:3, pages 133-140.
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Franklin A. Davis, Seung Lee, Huiming Zhang & Dean L. Fanelli. (2000) Applications of the Sulfinimine-Mediated Asymmetric Strecker Synthesis to the Synthesis of α-Alkyl α-Amino Acids. The Journal of Organic Chemistry 65:25, pages 8704-8708.
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Thomas Wirth. 2000. Organic Synthesis Highlights IV. Organic Synthesis Highlights IV 26 33 .
Eric Leclerc, Pierre Mangeney & Vivien Henryon. (2000) Enhancement of the diastereoselectivity in the addition of trimethylsilyl cyanide to chiral aldimines by catalysis with a chiral 1,2-diamine: unexpected mechanistic results. Tetrahedron: Asymmetry 11:17, pages 3471-3474.
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Shū Kobayashi & Haruro Ishitani. (1999) Catalytic Enantioselective Addition to Imines. Chemical Reviews 99:5, pages 1069-1094.
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John Tulinsky, B. Vernon Cheney, Stephen A. Mizsak, William Watt, Fusan Han, Lester A. Dolak, Thomas Judge & Ronald B. Gammill. (1998) Novel Asymmetric Synthesis of Atropisomeric 6-Aryl Pyrazinones via an Unusual Chirality Transfer Process. The Journal of Organic Chemistry 64:1, pages 93-100.
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Carlos Cativiela & Marı́a Dolores Dı́az-de-Villegas. (1998) Stereoselective synthesis of quaternary α-amino acids. Part 1: Acyclic compounds. Tetrahedron: Asymmetry 9:20, pages 3517-3599.
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AndréB Charette & Christophe Mellon. (1998) Enantioselective synthesis of α,α-disubstituted-α-amino acids by a sequential nucleophilic addition to nitriles. Tetrahedron 54:35, pages 10525-10535.
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Denice M. Spero & Suresh R. Kapadia. (1997) A Novel Method for the Asymmetric Synthesis of α,α-Disubstituted Alkylamines via Grignard Additions to Ketimines . The Journal of Organic Chemistry 62:16, pages 5537-5541.
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Thomas Wirth. (2003) New Strategies to α‐Alkylated α‐Amino Acids. Angewandte Chemie International Edition in English 36:3, pages 225-227.
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Thomas Wirth. (2006) Neue Strategien zu α‐alkylierten α‐Aminosäuren. Angewandte Chemie 109:3, pages 235-237.
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Franz-Josef Volk & August Wilhelm Frahm. (1996) Asymmetric Strecker Synthesis of the Four α-Quaternary 1-Amino-2-methylcyclohexanecarboxylic Acids. Liebigs Annalen 1996:11, pages 1893-1903.
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Mani S. Iyer, Kenneth M. Gigstad, Nivedita D. Namdev & Mark Lipton. (1996) Asymmetric Catalysis of the Strecker Amino Acid Synthesis by a Cyclic Dipeptide. Journal of the American Chemical Society 118:20, pages 4910-4911.
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Denice M. Spero & Suresh R. Kapadia. (1996) Enantioselective Synthesis of α,α-Disubstituted Amino Acid Derivatives via Enzymatic Resolution:  Preparation of a Thiazolyl-Substituted α-Methyl α-Benzyl Amine . The Journal of Organic Chemistry 61:21, pages 7398-7401.
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Horst Kunz, Wilfried Sager, Dirk Schanzenbach & Mathias Decker. (2006) Carbohydrates as chiral templates: Stereoselective Strecker synthesis of D‐α‐amino nitriles and acids using O ‐pivaloylated D ‐galactosylamine as the auxiliary . Liebigs Annalen der Chemie 1991:7, pages 649-654.
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Heinz Heimgartner. (2003) 3‐Amino‐2 H ‐Azirines. Synthons for α,α‐Disubstituted α‐Amino Acids in Heterocycle and Peptide Synthesis [New Analytical Methods (43)] . Angewandte Chemie International Edition in English 30:3, pages 238-264.
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Heinz Heimgartner. (2006) 3‐Amino‐2 H ‐azirine, Bausteine für α,α‐disubstituierte α‐Aminosäuren in Heterocyclen‐ und Peptidsynthesen . Angewandte Chemie 103:3, pages 271-297.
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Hiromichi Ohta, Yoichi Kimura & Yasushi Sugano. (1988) Kinetic resolution of ketone cyanohydrin acetates with a microbial enzyme. Tetrahedron Letters 29:52, pages 6957-6960.
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Horst Kunz, Wilfried Sager, Waldemar Pfrengle & Dirk Schanzenbach. (1988) Reversal of asymmetric induction in stereoselective strecker synthesis on galactosyl amine as the chiral matrix. Tetrahedron Letters 29:35, pages 4397-4400.
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K. Nebel & M Mutter. (1988) Stereoselective synthesis of isovaline (IVA) and IVA-containing dipeptldes for use in peptide synthesis 1. Tetrahedron 44:15, pages 4793-4796.
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Horst Kunz & Wilfried Sager. (2003) Diastereoselective Strecker Synthesis of α‐Aminonitriles on Carbohydrate Templates. Angewandte Chemie International Edition in English 26:6, pages 557-559.
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Horst Kunz & Wilfried Sager. (1987) Diastereoselektive Strecker-Synthese von α-Aminonitrilen an Kohlenhydrat-Matrices. Angewandte Chemie 99:6, pages 595-597.
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P. K. SUBRAMANIAN & R. W. WOODARD. (2016) ChemInform Abstract: An Asymmetric Strecker Synthesis of (R)‐(+)‐2‐Methyl‐3‐phenylalanine: An Efficient Preparation.. Chemischer Informationsdienst 17:32.
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