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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 21, 1991 - Issue 1
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Original Articles

A Safe, Simple, One-Pot Preparation of N-Derivatized β-Amino Alcohols and Oxazolidinones from Amino Acids

Arlene Correa Université Joseph Fourier de Grenoble, LEDSS, Bât. 52, 38041, Grenoble, Cedex, France
,
Jean-Noël Denis Université Joseph Fourier de Grenoble, LEDSS, Bât. 52, 38041, Grenoble, Cedex, France
&
Andrew E. Greene Université Joseph Fourier de Grenoble, LEDSS, Bât. 52, 38041, Grenoble, Cedex, France
Pages 1-9 | Received 22 Oct 1990, Published online: 24 Sep 2006

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Monika Simon, Andreea Micle, Valentin Badea & Carol Csunderlik. (2009) Bis(O-nitrophenyl) Carbonate as a New Reagent for the Synthesis of Chiral Oxazolidin-2-ones. Synthetic Communications 39:15, pages 2633-2639.
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Articles from other publishers (33)

Shaoqu Xie & Zhuoxi Li. (2023) Closing carbon and nitrogen cycles and addressing a critical global challenge: From seafood waste to sustainable chemicals. Journal of Cleaner Production 388, pages 135931.
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D. Manikandan, J. Swaminathan, S. Sharmila Tagore, S. Gomathi, N. Sabarinathan, M. Ramalingam, K. Balasubramani & V. Sethuraman. (2020) Crystallographic, spectral and computational studies on (S)-4-(4-aminobenzyl) oxazolidin-2-one. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 239, pages 118484.
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Sebastian Essig, Björn Schmalzbauer, Sebastian Bretzke, Olga Scherer, Andreas Koeberle, Oliver Werz, Rolf Müller & Dirk Menche. (2016) Predictive Bioinformatic Assignment of Methyl-Bearing Stereocenters, Total Synthesis, and an Additional Molecular Target of Ajudazol B. The Journal of Organic Chemistry 81:4, pages 1333-1357.
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FanHua Meng, Ning Chen & JiaXi Xu. (2012) An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides. Science China Chemistry 55:12, pages 2548-2553.
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Karina Thorn, Carsten Uhd Nielsen, Palle Jakobsen, Bente Steffansen, Charles K. Zercher & Mikael Begtrup. (2011) The tandem chain extension aldol reaction used for synthesis of ketomethylene tripeptidomimetics targeting hPEPT1. Bioorganic & Medicinal Chemistry Letters 21:15, pages 4597-4601.
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Luiz C. Dias, Juliana Fattori, Carla C. Perez, Vanda M. de Oliveira & Andrea M. Aguilar. (2008) An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols. Tetrahedron 64:25, pages 5891-5903.
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David Benoit, Elliot Coulbeck, Jason Eames & Majid Motevalli. (2008) On the structure and chiroptical properties of (S)-4-isopropyl-oxazolidin-2-one. Tetrahedron: Asymmetry 19:9, pages 1068-1077.
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Guangyu Xu, Yi Zhou, Chunhao Yang & Yuyuan Xie. (2008) A convenient synthesis of oxazolidinone derivatives linezolid and eperezolid from ( S )‐glyceraldehyde acetonide . Heteroatom Chemistry 19:3, pages 316-319.
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David A. Evans, Annette S. Kim, Troels Skrydstrup & Rolf H. Taaning. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Kun Xiao, Xin Li, Jingya Li, Lanping Ma, Bin Hu, Haiping Yu, Yan Fu, Rui Wang, Zeqiang Ma, Beiying Qiu, Jia Li, Dingyu Hu, Xin Wang & Jingkang Shen. (2006) Design, synthesis, and evaluation of Leu∗Ala hydroxyethylene-based non-peptide β-secretase (BACE) inhibitors. Bioorganic & Medicinal Chemistry 14:13, pages 4535-4551.
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Vítězslav Maier, Jana Horáková, Jan Petr, Dušan Drahoňovský & Juraj Ševčík. (2006) Using of S-(−)-2-hydroxymethyl-1,1-dimethylpyrrolidinium tetrafluoroborate as additive to the background electrolyte in capillary electrophoresis. Journal of Chromatography A 1103:2, pages 337-343.
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Paul Müller & David Riegert. (2005) Desymmetrization of spiro-activated meso-cyclopropanes via nucleophilic substitution. Tetrahedron 61:18, pages 4373-4379.
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Lanchi VoJames CiulaOwen W. Gooding. (2003) Chemical Development on the Chiral Auxiliary ( S )-4-(Phenylmethyl)-2-oxazolidinone Utilizing Automated Synthesis and DoE . Organic Process Research & Development 7:4, pages 514-520.
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Claudio Palomo, Jesus M. Aizpurua, Iraida Loinaz, Maria Jose Fernandez-Berridi & Lourdes Irusta. (2001) Scavenging of Fluorinated N , N ‘ -Dialkylureas by Hydrogen Binding:  A Novel Separation Method for Fluorous Synthesis . Organic Letters 3:15, pages 2361-2364.
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Owen W. GoodingThomas LindbergWendy MillerEdward MunyakLanchi Vo. (2001) Case Studies in Process Screening and Optimization Utilizing a New Automated Reactor−Analysis System. Organic Process Research & Development 5:3, pages 283-293.
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David A. Evans & Annette S. Kim. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Yikang Wu & Xin Shen. (2000) A high-yielding low-cost facile synthesis of 2-oxazolidinones chiral auxiliaries. Tetrahedron: Asymmetry 11:21, pages 4359-4363.
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Claire Sperandio, Jean-Noël Denis, Marie-Thérèse Averbuch-Pouchot & Yannick Vallée. (1998) Synthesis and crystal structure of (S)-(+)-2-[(1,1-dimethylethoxy)carbonyl] amino-2-phenylethanol. Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry 1:11, pages 709-714.
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Frank Schieweck & Hans-Josef Altenbach. (1998) Preparation of S-(−)-2-acetoxymethyl-2,5-dihydrofuran and S-(−)-N-Boc-2-hydroxymethyl-2,5-dihydropyrrole by enzymatic resolution. Tetrahedron: Asymmetry 9:3, pages 403-406.
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Dieter Schinzer, Anja Limberg & Oliver M. Böhm. (2006) Studies Towards the Total Synthesis of Epothilones: Asymmetric Synthesis of the Key Fragments. Chemistry – A European Journal 2:11, pages 1477-1482.
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David J. Ager, Indra Prakash & David R. Schaad. (1996) 1,2-Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. Chemical Reviews 96:2, pages 835-876.
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Subhash C. Sinha & Ehud Keinan. (1996) α-Multistriatin: The First Total Synthesis of a Natural Product via Antibody Catalysis. Israel Journal of Chemistry 36:2, pages 185-193.
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Romualdo Caputo, Ersilia Cassano, Luigi Longobardo & Giovanni Palumbo. (1995) Synthesis of Enantiopure N-and C-Protected homo-β-Amino Acids by Direct Homologation of α-Amino Acids ¶. Tetrahedron 51:45, pages 12337-12350.
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Kevin E.B. Parkes & Stewart K. Richardson. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1 52 .
Christoph M. Huwe & Siegfried Blechert. (1994) One pot synthesis of N-derivatized 2-oxazolidinones from amino alcohol carbamates. Tetrahedron Letters 35:51, pages 9533-9536.
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Mark A. Scialdone & A.I. Meyers. (1994) A stereoselective concise synthesis of C2- and meso-aminodiols from (R)-phenylglycinol. Tetrahedron Letters 35:41, pages 7533-7536.
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S. Hahn & P. Pachaly. (1994) P102 new synthesis of non-proteinogenic trans-3-arylprolines. European Journal of Pharmaceutical Sciences 2:1-2, pages 144.
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Claude Agami, François Couty, Louis Hamon & Olivier Venier. (1993) Chiral oxazolidinones from N-Boc derivatives of β-amino alcohols. Effect of a N-methyl substituent on reactivity and stereoselectivity. Tetrahedron Letters 34:28, pages 4509-4512.
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Hatsuo Maeda, Toshihide Maki & Hidenobu Ohmori. (1992) One-step transformation of α-amino acids to α-amino aldehydes effected by electrochemical oxidation of Ph3P. Tetrahedron Letters 33:10, pages 1347-1350.
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A. CORREA, J.‐N. DENIS & A. E. GREENE. (2010) ChemInform Abstract: A Safe, Simple, One‐Pot Preparation of N‐Derivatized β‐Amino Alcohols and Oxazolidinones from Amino Acids.. ChemInform 22:42.
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