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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 3
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Original Articles

Enantioselective Epoxidation of α,β-Unsaturated Ketones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts

Dae Young Kim Department of Chemistry, Soonchunhyang University, Asan, Chungnam, KoreaCorrespondence[email protected]
,
Young Jae Choi Department of Chemistry, Soonchunhyang University, Asan, Chungnam, Korea
,
Hai Yoon Park Department of Chemistry, Soonchunhyang University, Asan, Chungnam, Korea
,
Chang Ung Joung Department of Chemistry, Soonchunhyang University, Asan, Chungnam, Korea
,
Kwang Oh Koh Department of Chemistry, Soonchunhyang University, Asan, Chungnam, Korea
,
Joo Yang Mang Department of Chemistry, Soonchunhyang University, Asan, Chungnam, Korea
&
Kang-Yeoun Jung Department of Industrial Chemistry, Kangnung National University, Kangnung, Korea
 show all
Pages 435-443 | Received 22 Oct 2001, Published online: 17 Aug 2006

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NosratO. Mahmoodi, MohammadR. Yazdanbakhsh & Fateme Ghanbari. (2010) Epoxidation of 1,4-Diaroyl Ethene Derivatives in the Presence of UHP or H2O2 . Synthetic Communications 40:21, pages 3181-3185.
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Articles from other publishers (45)

Kyeong Seop Kim & Dae Young Kim. (2023) Organocatalytic Enantioselective One‐pot Synthesis of Dihydrocoumarins via C−H Oxidation and Cyclization Cascade. Asian Journal of Organic Chemistry 12:10.
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Mona A. Shalaby, Sameh A. Rizk & Asmaa M. Fahim. (2023) Synthesis, reactions and application of chalcones: a systematic review. Organic & Biomolecular Chemistry 21:26, pages 5317-5346.
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Mohammed Salim Mohammed, Homa Targhan & Kiumars Bahrami. (2023) Design and introduction of quaternary ammonium hydroxide‐functionalized graphene oxide quantum dots as a pseudo-homogeneous catalyst for epoxidation of α,β-unsaturated ketones. Scientific Reports 13:1.
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Greta G. Zámbó, Jonas F. Schlagintweit, Robert M. Reich & Fritz E. Kühn. (2022) Organometallic 3d transition metal NHC complexes in oxidation catalysis. Catalysis Science & Technology 12:16, pages 4940-4961.
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Mohamed Shaker S. Adam, Saad Shaaban & Nashwa M. El‐Metwaly. (2022) Two ionic oxo‐vanadate and dioxo‐molybdate complexes of dinitro‐aroylhydrazone derivative: Effective catalysts for epoxidation reactions, biological activity, ctDNA binding, density functional theory, and in silico investigations . Applied Organometallic Chemistry 36:8.
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Mohamed Shaker S. Adam & Ahmed Khalil. (2022) Nickel (II), copper (II), and vanadyl (II) complexes with tridentate nicotinoyl hydrazone derivative functionalized as effective catalysts for epoxidation processes and as biological reagents. Journal of the Taiwan Institute of Chemical Engineers 132, pages 104192.
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Eva‐Maria H. J. Esslinger, Jonas F. Schlagintweit, Greta G. Zámbó, Alexander M. Imhof, Robert M. Reich & Fritz E. Kühn. (2021) The Effect of trans Axial Isocyanide Ligands on Iron(II) Tetra‐NHC Complexes and their Reactivity in Olefin Epoxidation . Asian Journal of Organic Chemistry 10:10, pages 2654-2662.
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Marco A. Bernd, Florian Dyckhoff, Benjamin J. Hofmann, Alexander D. Böth, Jonas F. Schlagintweit, Jens Oberkofler, Robert M. Reich & Fritz E. Kühn. (2020) Tuning the electronic properties of tetradentate iron-NHC complexes: Towards stable and selective epoxidation catalysts. Journal of Catalysis 391, pages 548-561.
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Deepak P Mahajan, Himanshu M Godbole, Girij P Singh & Gautham G Shenoy. (2019) Synthesis of novel phase transfer catalysts derived from proline-mandelic acid/tartaric acid: their evaluation in enantioselective epoxidation and Darzen condensation. Journal of Chemical Sciences 131:3.
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Hye Im Jung, Jin Hwa Park & Dae Young Kim. (2018) Enantioselective Organocatalytic Mannich Reaction and Fluorination Sequence of Pyrazolones to Isatin‐derived Ketimines. Bulletin of the Korean Chemical Society 39:12, pages 1442-1448.
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Richard C. LarockRichard C. Larock & Tanay Kesharwani. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 11 104 .
Kaveh Khosravi, Shirin Naserifar & Boshra Mahmoudi. (2017) Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant. Journal of the Chinese Chemical Society 64:6, pages 683-689.
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Kaveh Khosravi & Shirin Naserifar. (2016) Facile epoxidation of α, β-unsaturated ketones with urea-2,2-dihydroperoxypropane as a new oxidant. Journal of the Iranian Chemical Society 14:2, pages 323-328.
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Guoqiang Yang, Huiyuan Du, Jia Liu, Zheng Zhou, Xingbang Hu & Zhibing Zhang. (2017) Oxidation of olefins using molecular oxygen catalyzed by a part per million level of recyclable copper catalyst under mild conditions. Green Chemistry 19:3, pages 675-681.
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Wei He, Zheng Fang, Qitao Tian, Weidong Shen & Kai Guo. (2016) Tandem, Effective Continuous Flow Process for the Epoxidation of Cyclohexene. Industrial & Engineering Chemistry Research 55:5, pages 1373-1379.
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Yingguang Zhu, Qian Wang, Richard G. Cornwall & Yian Shi. (2014) Organocatalytic Asymmetric Epoxidation and Aziridination of Olefins and Their Synthetic Applications. Chemical Reviews 114:16, pages 8199-8256.
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Saeed Rayati & Payam Abdolalian. (2013) Sonochemical syntheses of nano-sized dioxomolybdenum complexes: An efficient, selective and reusable heterogeneous nanocatalyst for oxidation of alkenes. Applied Catalysis A: General 456, pages 240-248.
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S. Shaun Murphree. 2011. Modern Heterocyclic Chemistry. Modern Heterocyclic Chemistry 11 162 .
Young Ku Kang, Bo Kyung Kwon, Joo Yang Mang & Dae Young Kim. (2011) Chiral Pd-catalyzed enantioselective Friedel–Crafts reaction of indoles with γ,δ-unsaturated β-keto phosphonates. Tetrahedron Letters 52:25, pages 3247-3249.
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You-Kyung Kwon, Young-Ku Kang & Dae-Young Kim. (2011) Microwave-Assisted Organocatalytic Synthesis of Tetrahydroquinolines via Hydride Transfer and Cyclization. Bulletin of the Korean Chemical Society 32:5, pages 1773-1776.
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Seung Hee Kang & Dae Young Kim. (2010) Catalytic Enantioselective Fluorination of α‐Chloro‐β‐keto Esters in the Presence of Chiral Nickel Complexes. Advanced Synthesis & Catalysis 352:16, pages 2783-2786.
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Attila Makó, Zsolt Rapi, György Keglevich, Áron Szöllősy, László Drahos, László Hegedűs & Péter Bakó. (2010) Asymmetric epoxidation of substituted chalcones and chalcone analogues catalyzed by α-d-glucose- and α-d-mannose-based crown ethers. Tetrahedron: Asymmetry 21:8, pages 919-925.
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Young Ku Kang & Dae Young Kim. (2009) Organocatalytic Highly Enantio- and Diastereoselective Mannich Reaction of β-Ketoesters with N -Boc-aldimines . The Journal of Organic Chemistry 74:15, pages 5734-5737.
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Ju Hee Lee & Dae Young Kim. (2009) Enantio‐ and Diastereoselective Mannich‐Type Reactions of α‐Cyano Ketones with N ‐Boc Aldimines Catalyzed by Chiral Bifunctional Urea . Advanced Synthesis & Catalysis 351:11-12, pages 1779-1782.
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. (2009) Palladium-catalyzed Asymmetric Mannich-type Reactions of α-Cyanoketones with N-Boc Aldimines. Bulletin of the Korean Chemical Society 30:7, pages 1437-1438.
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Seung Hee Kang, Young Ku Kang & Dae Young Kim. (2009) Catalytic enantioselective conjugate addition of aromatic amines to fumarate derivatives: asymmetric synthesis of aspartic acid derivatives. Tetrahedron 65:29-30, pages 5676-5679.
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. (2009) Enantioselective Fluorination of β-Keto Phosphonates and β-Ketoesters Catalyzed by Chiral Palladium Complexes. Bulletin of the Korean Chemical Society 30:4, pages 829-836.
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Hong Jin, Haoyu Zhao, Feihu Zhao, Shihong Li, Wei Liu, Guoping Zhou, Ke Tao & Taiping Hou. (2009) Efficient epoxidation of chalcones with urea-hydrogen peroxide under ultrasound irradiation. Ultrasonics Sonochemistry 16:3, pages 304-307.
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. (2009) Catalytic Asymmetric Electrophilic α-Amination of β-Ketoesters in the Presence of Chiral Nickel Complexes. Bulletin of the Korean Chemical Society 30:1, pages 249-252.
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. (2008) Enantioselective Electrophilic α-Amination of α-Cyanoketones Catalyzed by Chiral Nickel Complexes. Bulletin of the Korean Chemical Society 29:10, pages 2036-2038.
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Sun Hee Jung & Dae Young Kim. (2008) Catalytic enantioselective electrophilic α-hydrazination of β-ketoesters using bifunctional organocatalysts. Tetrahedron Letters 49:38, pages 5527-5530.
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G. Dake. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 173 233 .
. (2007) Catalytic Enantioselective Fluorination Reactions of α-Cyano Acetates and α-Cyanophosphonates Using Chiral Palladium Complexes. Bulletin of the Korean Chemical Society 28:12, pages 2435-2441.
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. (2007) Catalytic Asymmetric Fluorination of α-Chloro-β-ketoesters in the Presence of Chiral Palladium Complexes. Bulletin of the Korean Chemical Society 28:12, pages 2191-2192.
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Barry Lygo, Stuart D. Gardiner, Michael C. McLeod & Daniel C. M. To. (2007) Diastereo- and enantioselective synthesis of α,β-epoxyketones using aqueous NaOCl in conjunction with dihydrocinchonidine derived phase-transfer catalysis at room temperature. Scope and limitations. Org. Biomol. Chem. 5:14, pages 2283-2290.
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Young Ku Kang & Dae Young Kim. (2006) Catalytic enantioselective electrophilic α-amination of β-ketoesters catalyzed by chiral palladium complexes. Tetrahedron Letters 47:27, pages 4565-4568.
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. (2006) Asymmetric Michael Reaction of Malonate Derivatives with α,β-Unsaturated Ketones Using Chiral Quaternary Ammonium Salts. Bulletin of the Korean Chemical Society 27:6, pages 857-862.
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. (2006) Asymmetric Electrophilic Fluorination of β-Keto Phosphonates in Ionic Liquid Media Catalyzed by Chiral Palladium Complexes. Bulletin of the Korean Chemical Society 27:3, pages 423-425.
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Albert Padwa & Shaun Murphree. 2005. A critical review of the 2003 literature preceded by two chapters on current heterocyclic topics. A critical review of the 2003 literature preceded by two chapters on current heterocyclic topics 54 81 .
. (2004) Catalytic Enantioselective Fluorination of α-Cyano Esters by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts. Bulletin of the Korean Chemical Society 25:10, pages 1451-1452.
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Peter I. Dalko & Lionel Moisan. (2004) Im Goldenen Zeitalter der Organokatalyse. Angewandte Chemie 116:39, pages 5248-5286.
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Eun Joo Park, Mi Hee Kim & Dae Young Kim. (2004) Enantioselective Alkylation of β-Keto Esters by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salts. The Journal of Organic Chemistry 69:20, pages 6897-6899.
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. (2004) Poly(ethylene glycol) Supported Chiral Quaternary Ammonium Salts as Phase-Transfer Catalysts for Catalytic Enantioselective Synthesis of α-Amino Acids. Bulletin of the Korean Chemical Society 25:3, pages 347-348.
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. (2003) Enantioselective Michael Reaction of Fluoromalonates and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salt. Bulletin of the Korean Chemical Society 24:10, pages 1425-1426.
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Dae Young Kim, Young Jae Choi, Hai Yoon Park, Chang Ung Joung, Kwang Oh Koh, Joo Yang Mang & Kang‐Yeoun Jung. (2003) Enantioselective Epoxidation of α,β‐Unsaturated Ketones by Phase‐Transfer Catalysis Using Chiral Quaternary Ammonium Salts.. ChemInform 34:27.
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