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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 10
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Original Articles

Decarboxylation of α-Amino Acids Containing Two and Three Stereogenic Centers: A Simple One-Step Procedure to Prepare two Optically Active β-Amino Alcohols and a Bicyclic Pyrrolidine Derivative

Sabine Wallbaum Fachbereich Chemie, Universität Oldenburg, Ammerländer Heerstraße 114-118 D-26129, Oldenburg i.O., Germany
,
Thomas Mehler Fachbereich Chemie, Universität Oldenburg, Ammerländer Heerstraße 114-118 D-26129, Oldenburg i.O., Germany
&
Jürgen Martens Fachbereich Chemie, Universität Oldenburg, Ammerländer Heerstraße 114-118 D-26129, Oldenburg i.O., Germany
Pages 1381-1387 | Received 20 Oct 1993, Published online: 23 Sep 2006

Citations (24)

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Jürgen Martens & Ravi Bhushan. (2023) Direct Thin Layer Chromatographic Enantioseparation of Active Pharmaceutical Ingredients via Non-Covalent Diastereomers. Separation & Purification Reviews 0:0, pages 1-19.
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Jörg Wilken & Jürgen Martens. (1996) Enantioselective Catalytic Borane Reduction of Prochiral Ketones: Synthesis and Application of New Rigid β-Amino Alcohols with a Cycloalkanol Subunit. Synthetic Communications 26:23, pages 4477-4485.
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Articles from other publishers (22)

Oleg I. Afanasyev, Evgeniya Podyacheva, Alexander Rudenko, Alexey A. Tsygankov, Maria Makarova & Denis Chusov. (2020) Redox Condensations of o -Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family . The Journal of Organic Chemistry 85:14, pages 9347-9360.
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Laurens Claes, Michiel Janssen & Dirk E. De Vos. (2019) Organocatalytic Decarboxylation of Amino Acids as a Route to Bio‐based Amines and Amides. ChemCatChem 11:17, pages 4297-4306.
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Free De Schouwer, Laurens Claes, Annelies Vandekerkhove, Jasper Verduyckt & Dirk E. De Vos. (2019) Protein‐Rich Biomass Waste as a Resource for Future Biorefineries: State of the Art, Challenges, and Opportunities. ChemSusChem 12:7, pages 1272-1303.
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Son Q. Pham, Pengfei Gao & Zhi Li. (2013) Engineering of recombinant E. coli cells co-expressing P450pyrTM monooxygenase and glucose dehydrogenase for highly regio- and stereoselective hydroxylation of alicycles with cofactor recycling . Biotechnology and Bioengineering 110:2, pages 363-373.
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Achim Häußermann, Frank Rominger & Bernd F. Straub. (2012) CO 2 on a Tightrope: Stabilization, Room‐Temperature Decarboxylation, and Sodium‐Induced Carboxylate Migration . Chemistry – A European Journal 18:44, pages 14174-14185.
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Pietro Campiglia, Claudio Aquino, Alessia Bertamino, Nicoletta De Simone, Marina Sala, Sabrina Castellano, Marisabella Santoriello, Paolo Grieco, Ettore Novellino & Isabel M. Gomez-Monterrey. (2010) Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based α,α-amino esters. Org. Biomol. Chem. 8:3, pages 622-627.
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Christopher J. Wolyniak, Gavin L. Sacks, Bruce S. Pan & J. Thomas Brenna. (2005) Carbon Position-Specific Isotope Analysis of Alanine and Phenylalanine Analogues Exhibiting Nonideal Pyrolytic Fragmentation. Analytical Chemistry 77:6, pages 1746-1752.
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Zhi Li, Hans-Jürgen Feiten, Dongliang Chang, Wouter A. Duetz, Jan B. van Beilen & Bernard Witholt. (2001) Preparation of ( R )- and ( S )- N -Protected 3-Hydroxypyrrolidines by Hydroxylation with Sphingomonas sp. HXN-200, a Highly Active, Regio- and Stereoselective, and Easy to Handle Biocatalyst . The Journal of Organic Chemistry 66:25, pages 8424-8430.
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Helmut Pennemann, Sabine Wallbaum & Jürgen Martens. (2000) Diastereoselective hydroboration of chiral enamines using an enantiomerically pure amine from an industrial waste material as the source of chirality. Tetrahedron: Asymmetry 11:10, pages 2133-2142.
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R. Bhushan, J. Martens & G.Thuku Thiongo. (2000) Direct thin layer chromatography enantioresolution of some basic dl-amino acids using a pharmaceutical industry waste as chiral impregnating reagent. Journal of Pharmaceutical and Biomedical Analysis 21:6, pages 1143-1147.
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Michael Kossenjans & Jürgen Martens. (1999) Highly stereoselective synthesis of 1,3-aminoalcohols via Mannich reactions. Tetrahedron: Asymmetry 10:17, pages 3409-3416.
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Zhi Li, Hans-Jürgen Feiten, Jan B van Beilen, Wouter Duetz & Bernard Witholt. (1999) Preparation of optically active N-benzyl-3-hydroxypyrrolidine by enzymatic hydroxylation. Tetrahedron: Asymmetry 10:7, pages 1323-1333.
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Jörg Wilken, Claire Thorey, Harald Gröger, Detlev Haase, Wolfgang Saak, Siegfried Pohl, Jacques Muzart & Jürgen Martens. (1997) Utilization of Industrial Waste Materials, 11. Synthesis of New, Chiral β-sec-Amino Alcohols – Diastereodivergent Addition of Grignard Reagents to α-Amino Aldehydes Based on the (all-R)-2-Azabicyclo[3.3.0]octane System. Liebigs Annalen 1997:10, pages 2133-2146.
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R. Bhushan, J. Martens, Sabine Wallbaum, Shalini Joshi & Vineeta Parshad. (1997) TLC resolution of enantiomers of amino acids and dansyl derivatives using (1R,3R,5R)-2-azabicyclo[3,3,0]octan-3-carboxylic acid as impregnating reagent. Biomedical Chromatography 11:5, pages 286-288.
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Jörg Wilken, Harald Gröger, Michael Kossenjans & Jürgen Martens. (1997) Synthesis and application of new (threo)- and (erythro)-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde. Tetrahedron: Asymmetry 8:16, pages 2761-2771.
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Jörg Wilken & Jürgen Martens. (1997) Utilization of Industrial Waste Materials, 7. – Synthesis of New, Chiral β-sec-Amino Alcohols – Regio- and Diastereoselective α-Hydroxyalkylation of (1R,5R)-2-Azabicyclo[3.3.0]octane. Liebigs Annalen 1997:3, pages 563-571.
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Hans Jürgen Veith, Markus Collas & Reinhold Zimmer. (1997) Simple Synthesis of Both Enantiomers of 3-Methyl-N-(3-Methylbutyl)pyrrolidine. Liebigs Annalen 1997:2, pages 391-394.
Crossref
Raymond McCague & Guy Casy. 1997. 203 261 .
J. Eilers, J. Wilken & J. Martens. (1996) Syntheses of new chiral 1,2-diamines and δ-amino-alcohols and their application in catalytic enantioselective CC bond formations at an elevated temperature of up to 110 °C. Tetrahedron: Asymmetry 7:8, pages 2343-2357.
Crossref
Jörg Wilken, Sabine Wallbaum, Wolfgang Saak, Detlef Haase, Siegfried Pohl, Jürgen Martens, Laxmikant N. Patkar, Arun N. Dixit, Pabba Chittari & Srinivasachari Rajappa. (2006) Utilization of Industrial Waste Materials, 6. Utilization of Derivatives of the Bicyclic Proline Analog ( all‐R )‐Octahydrocyclopenta[ b ]pyrrol‐2‐carboxylic Acid in the Stereoselective Synthesis . Liebigs Annalen 1996:6, pages 927-934.
Crossref
Michael D. Ennis, Robert L. Hoffman, Nabil B. Ghazal, David W. Old & Pamela A. Mooney. (1996) Asymmetric Synthesis of Cis -Fused Bicyclic Pyrrolidines and Pyrrolidinones via Chiral Polycyclic Lactams . The Journal of Organic Chemistry 61:17, pages 5813-5817.
Crossref
S. WALLBAUM, T. MEHLER & J. MARTENS. (2010) ChemInform Abstract: Decarboxylation of α‐Amino Acids Containing Two and Three Stereogenic Centers (I), (III): A Simple One‐Step Procedure to Prepare Two Optically Active β‐Amino Alcohols, e.g. (II), and a Bicyclic Pyrrolidine Derivative (IV).. ChemInform 25:48.
Crossref

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