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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 8
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Original Articles

Synthesis of R- and S- Fluoxetine, Norfluoxetine and Related Compounds from Styrene Oxide

David Mitchell Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana, 46285
&
Thomas M. Koenig Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana, 46285
Pages 1231-1238 | Received 13 Oct 1994, Published online: 23 Sep 2006

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Matthias Schulze. (2010) Synthesis of 2-Arylethylamines by the Curtius Rearrangement. Synthetic Communications 40:10, pages 1461-1476.
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DonaldS. Risley, V.Scott Sharp & JohnR. Palmer. (1996) Evaluation of a New Pepsin Enzyme Chiral Stationary Phase for the Optimized Separation of Seproxetine (S-Norfluoxetine) from R-Norfluoxetine. Journal of Liquid Chromatography & Related Technologies 19:3, pages 449-465.
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Articles from other publishers (36)

Xue-E Guan, Run-Ping Miao, Xia Hua, Xiao Jin, Guo-Zhong Deng, Bao-Dong Cui, Wen-Yong Han, Nan-Wei Wan & Yong-Zheng Chen. (2023) Biocatalytic Enantioselective Synthesis of Chiral β-Hydroxy Nitriles Using Cyanohydrins as Cyano Sources. ACS Catalysis 13:20, pages 13597-13606.
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Daijun Zheng & Yasuhisa Asano. (2020) Biocatalytic asymmetric ring-opening of dihydroisoxazoles: a cyanide-free route to complementary enantiomers of β-hydroxy nitriles from olefins. Green Chemistry 22:15, pages 4930-4936.
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Kok-Hou Tan, Anwar Iqbal, Farook Adam, N. H. H. Abu Bakar, M. N. Ahmad, Rahimi M. Yusop & Hariy Pauzi. (2019) Influence of Mg/CTAB ratio on the structural, physicochemical properties and catalytic activity of amorphous mesoporous magnesium silicate catalysts. RSC Advances 9:66, pages 38760-38771.
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Sajjad Keshipour, Mehran Kulaei & Fatemeh Ahour. (2017) Graphene Oxide Nano-Sheets-Supported Co(II)-d-Penicillamine as a Green and Highly Selective Catalyst for Epoxidation of Styrene. Iranian Journal of Science and Technology, Transactions A: Science 43:1, pages 85-94.
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Sajjad Keshipour & Masoumeh Khezerloo. (2017) Gold nanoparticles supported on cellulose aerogel as a new efficient catalyst for epoxidation of styrene. Journal of the Iranian Chemical Society 14:5, pages 1107-1112.
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Jèssica Margalef, Tove Slagbrand, Fredrik Tinnis, Hans Adolfsson, Montserrat Diéguez & Oscar Pàmies. (2016) Third‐Generation Amino Acid Furanoside‐Based Ligands from d ‐Mannose for the Asymmetric Transfer Hydrogenation of Ketones: Catalysts with an Exceptionally Wide Substrate Scope . Advanced Synthesis & Catalysis 358:24, pages 4006-4018.
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Sajjad Keshipour & Nastaran Kalam Khalteh. (2016) Oxidation of ethylbenzene to styrene oxide in the presence of cellulose‐supported Pd magnetic nanoparticles. Applied Organometallic Chemistry 30:8, pages 653-656.
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V. Arjunan, R. Anitha, L. Devi, S. Mohan & Haifeng Yang. (2015) Comprehensive quantum chemical and spectroscopic (FTIR, FT-Raman, 1H, 13C NMR) investigations of (1,2-epoxyethyl)benzene and (1,2-epoxy-2-phenyl)propane. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 135, pages 120-136.
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Michael Vogl, Regina Kratzer, Bernd Nidetzky & Lothar Brecker. (2012) Candida tenuis Xylose Reductase Catalyzed Reduction of Aryl Ketones for Enantioselective Synthesis of Active Oxetine Derivatives . Chirality 24:10, pages 847-853.
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Gopal L. Khatik, Varun Kumar & Vipin A. Nair. (2012) Reversal of Selectivity in Acetate Aldol Reactions of N -Acetyl-( S )-4-isopropyl-1-[( R )-1-phenylethyl]imidazolidin-2-one . Organic Letters 14:10, pages 2442-2445.
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Huiling Geng, Xiaowei Zhang, Mingxin Chang, Le Zhou, Wenjun Wu & Xumu Zhang. (2011) Ruthenium‐Catalyzed Asymmetric Hydrogenation of β‐Keto‐ enamines: An Efficient Approach to Chiral γ‐Amino Alcohols. Advanced Synthesis & Catalysis 353:16, pages 3039-3043.
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David M. Hodgson & Stanislav Man. (2011) Synthesis of the Anti‐HIV Agent (−)‐Hyperolactone C by Using Oxonium Ylide Formation–Rearrangement. Chemistry – A European Journal 17:35, pages 9731-9737.
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Randall W. Nowill, Trisha J. Patel, David L. Beasley, Jose A. Alvarez, Elizah JacksonIIIIII, Todd J. Hizer, Ion Ghiviriga, Scott C. Mateer & Brent D. Feske. (2011) Biocatalytic strategy toward asymmetric β-hydroxy nitriles and γ-amino alcohols. Tetrahedron Letters 52:19, pages 2440-2442.
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Neeraj Bala & Swapandeep Singh Chimni. (2010) Recent developments in the asymmetric hydrolytic ring opening of epoxides catalysed by microbial epoxide hydrolase. Tetrahedron: Asymmetry 21:24, pages 2879-2898.
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Kelsey L. Hanson, Brooke M. VandenBrink, Kantipudi N. Babu, Kyle E. Allen, Wendel L. Nelson & Kent L. Kunze. (2010) Sequential Metabolism of Secondary Alkyl Amines to Metabolic-Intermediate Complexes: Opposing Roles for the Secondary Hydroxylamine and Primary Amine Metabolites of Desipramine, ( S )-Fluoxetine, and N- Desmethyldiltiazem . Drug Metabolism and Disposition 38:6, pages 963-972.
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Mauro Panunzio, Emiliano Tamanini, Elisa Bandini, Eileen Campana, Antonio D'Aurizio & Paola Vicennati. (2006) 5-Phenylthio-1,3-oxazinan-4-ones via hetero Diels–Alder reactions: synthesis of (R)- and (S)-Duloxetines and Fluoxetines. Tetrahedron 62:52, pages 12270-12280.
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Awadhesh Kumar, Sumana SenGupta, K.K. Pushpa, P.D. Naik & P.N. Bajaj. (2006) Detection of OH on photolysis of styrene oxide at 193nm in gas phase. Chemical Physics Letters 430:4-6, pages 240-246.
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Meng-Yang Chang, Chun-Yu Lin & Chun-Li Pai. (2006) CAN-mediated oxidative cleavage of 4-aryl-3,4-dihydroxypiperidines. Tetrahedron Letters 47:15, pages 2565-2568.
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Yangzhou Li, Zhiming Li, Feng Li, Quanrui Wang & Fanggang Tao. (2005) Preparation of polymer-supported Ru-TsDPEN catalysts and use for enantioselective synthesis of (S)-fluoxetine. Organic & Biomolecular Chemistry 3:14, pages 2513.
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Pradeep Kumar, Rajesh Kumar Upadhyay & Rajesh Kumar Pandey. (2004) Asymmetric dihydroxylation route to (R)-isoprenaline, (R)-norfluoxetine and (R)-fluoxetine. Tetrahedron: Asymmetry 15:24, pages 3955-3959.
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Daniel D. Caspi, David C. Ebner, Jeffrey T. Bagdanoff & Brian M. Stoltz. (2004) The Resolution of Important Pharmaceutical Building Blocks by Palladium‐Catalyzed Aerobic Oxidation of Secondary Alcohols. Advanced Synthesis & Catalysis 346:2-3, pages 185-189.
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V. Ratovelomanana‐Vidal, C. Girard, R. Touati, J. P. Tranchier, B. Ben Hassine & J. P. Genêt. (2003) Enantioselective Hydrogenation of β‐Keto Esters using Chiral Diphosphine‐Ruthenium Complexes: Optimization for Academic and Industrial Purposes and Synthetic Applications. Advanced Synthesis & Catalysis 345:1-2, pages 261-274.
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Ahmed Kamal, G.B.Ramesh Khanna & R. Ramu. (2002) Chemoenzymatic synthesis2 of both enantiomers of fluoxetine, tomoxetine and nisoxetine: lipase-catalyzed resolution of 3-aryl-3-hydroxypropanenitriles. Tetrahedron: Asymmetry 13:18, pages 2039-2051.
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Rajesh Kumar Pandey, Rodney A. Fernandes & Pradeep Kumar. (2002) An asymmetric dihydroxylation route to enantiomerically pure norfluoxetine and fluoxetine. Tetrahedron Letters 43:25, pages 4425-4426.
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Masahito Watanabe, Kunihiko Murata & Takao Ikariya. (2002) Practical Synthesis of Optically Active Amino Alcohols via Asymmetric Transfer Hydrogenation of Functionalized Aromatic Ketones. The Journal of Organic Chemistry 67:5, pages 1712-1715.
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James W Hilborn, Zhi-Hui Lu, Alex R Jurgens, Q.Kevin Fang, Paul Byers, Stephen A Wald & Chris H Senanayake. (2001) A practical asymmetric synthesis of (R)-fluoxetine and its major metabolite (R)-norfluoxetine. Tetrahedron Letters 42:51, pages 8919-8921.
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Su-Dong Cho, Hyeung-Jae Kim, Chuljin Ahn, J.R. Falck & Dong-Soo Shin. (1999) The first preparation of α-functionalized benzylamine. Tetrahedron Letters 40:47, pages 8215-8217.
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M Perez, P.J Pauwels, I Pallard-Sigogneau, C Fourrier, P Chopin, C Palmier, V Colovray & S Halazy. (1998) Design and synthesis of new potent, silent 5-HT1A antagonists by covalent coupling of aminopropanol derivatives with selective serotonin reuptake inhibitors. Bioorganic & Medicinal Chemistry Letters 8:23, pages 3423-3428.
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Bridget D. Brandes & Eric N. Jacobsen. (1997) Synthesis of enantiopure 3-chlorostyrene oxide via an asymmetric epoxidation-hydrolytic kinetic resolution sequence. Tetrahedron: Asymmetry 8:23, pages 3927-3933.
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Gideon Grogan, Catherine Rippé & Andrew Willetts. (1997) Biohydrolysis of substituted styrene oxides by Beauveria densa CMC 3240. Journal of Molecular Catalysis B: Enzymatic 3:5, pages 253-257.
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Paul N Devine, Richard M HeidJr.Jr. & David M Tschaen. (1997) Stereoselective synthesis of 2-aryloxy esters: An asymmetric approach to fluoxetine, tomoxetine and nisoxetine. Tetrahedron 53:20, pages 6739-6746.
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G. Pattenden, J. I. G. Cadogan & S. V. LeyG. Pattenden, J. I. G. Cadogan & S. V. Ley. 1997. Dictionary of Organic Compounds. Dictionary of Organic Compounds 1 26 .
Hosang E.Master, R.V. Newadkar, R.A. Rane & Ashok Kumar. (1996) Highly efficient enzymatic resolution of homoallyl alcohols leading to a simple synthesis of optically pure fluoxetine and related compounds. Tetrahedron Letters 37:51, pages 9253-9254.
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Franz Bracher & Thomas Litz. (1996) An efficient chemoenzymatic route to the antidepressants (R)-fluoxetine and (R)-tomoxetine. Bioorganic & Medicinal Chemistry 4:6, pages 877-880.
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D. MITCHELL & T. M. KOENIG. (2010) ChemInform Abstract: Synthesis of R‐ and S‐Fluoxetine (VIII), Norfluoxetine (VI) and Related Compounds from Styrene Oxide.. ChemInform 26:31.
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