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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 33, 2003 - Issue 12
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Original Articles

“Instant Methylide” Modification of the Corey–Chaykovsky Epoxide Synthesis

James A. Ciaccio Department of Chemistry, Fordham University, Bronx, New York, USACorrespondence[email protected]
,
Antoinette L. Drahus Department of Chemistry, Fordham University, Bronx, New York, USA
,
Regina M. Meis Department of Chemistry, Fordham University, Bronx, New York, USA
,
Carice T. Tingle Department of Chemistry, Fordham University, Bronx, New York, USA
,
Michael Smrtka Department of Chemistry, Fordham University, Bronx, New York, USA
&
Richard Geneste Department of Chemistry, Fordham University, Bronx, New York, USA
Pages 2135-2143 | Received 17 Oct 2002, Published online: 17 Aug 2006

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James A. Ciaccio & Courtney E. Aman. (2006) “Instant Methylide” Modification of the Corey–Chaykovsky Cyclopropanation Reaction. Synthetic Communications 36:10, pages 1333-1341.
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Articles from other publishers (31)

Shruti S. Malunavar, Suraj M. Sutar, Pavankumar Prabhala, Hemantkumar M. Savanur, Rajesh G. Kalkhambkar, Gopalakrishnan Aridoss & Kenneth K. Laali. (2021) Facile synthesis of libraries of functionalized cyclopropanes and oxiranes using ionic liquids – A new approach to the classical Corey-Chaykovsky reaction. Tetrahedron Letters 81, pages 153339.
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Chengbo Yao, Tobias Dahmen, Andreas Gansäuer & Jack Norton. (2019) Anti-Markovnikov alcohols via epoxide hydrogenation through cooperative catalysis. Science 364:6442, pages 764-767.
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Gangarajula Sudhakar & Kovela Satish. (2015) Nazarov Cyclization of Divinyl and Arylvinyl Epoxides: Application in the Synthesis of Resveratrol‐Based Natural Products. Chemistry – A European Journal 21:17, pages 6475-6480.
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María J. Moure, Raul SanMartin & Esther Dominguez. (2012) Benzofurans from Benzophenones and Dimethylacetamide: Copper‐Promoted Cascade Formation of Furan O1C2 and C2C3 Bonds Under Oxidative Conditions. Angewandte Chemie International Edition 51:13, pages 3220-3224.
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María J. Moure, Raul SanMartin & Esther Dominguez. (2012) Benzofurans from Benzophenones and Dimethylacetamide: Copper‐Promoted Cascade Formation of Furan O1C2 and C2C3 Bonds Under Oxidative Conditions. Angewandte Chemie 124:13, pages 3274-3278.
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S. Shaun Murphree. 2011. Modern Heterocyclic Chemistry. Modern Heterocyclic Chemistry 11 162 .
Sarah A. Kavanagh, Alessandro Piccinini & Stephen J. Connon. (2010) Efficient Catalytic Corey–Chaykovsky Reactions Involving Ketone Substrates. Advanced Synthesis & Catalysis 352:11‐12, pages 2089-2093.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents.
James A. Ciaccio, Elena L. Guevara, Rabeka Alam & Christina D. D’agrosa. (2010) Probing the Reactivity of Dimethylsulfoxonium Methylide with Conjugated and Nonconjugated Carbonyl Compounds: An Undergraduate Experiment Combining Synthesis, Spectral Analysis, and Mechanistic Discovery. Journal of Chemical Education 87:8, pages 850-853.
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Zheng Li, Zhao-Li Zhou, Ze-Hong Miao, Li-Ping Lin, Hui-Jin Feng, Lin-Jiang Tong, Jian Ding & Yuan-Chao Li. (2009) Design and Synthesis of Novel C14-Hydroxyl Substituted Triptolide Derivatives as Potential Selective Antitumor Agents. Journal of Medicinal Chemistry 52:16, pages 5115-5123.
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Pattama Saisaha, Chakkrapan Nerungsi, Supitchaya Iamsaard & Tienthong Thongpanchang. (2009) Pyridine stabilized oxiranyl remote anions. Tetrahedron Letters 50:29, pages 4217-4220.
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David C. Forbes, Sampada V. Bettigeri, Samit A. Patrawala, Susanna C. Pischek & Michael C. Standen. (2009) S-Methylidene agents: preparation of chiral non-racemic heterocycles. Tetrahedron 65:1, pages 70-76.
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Wilma Quaglia, Alessandro Piergentili, Fabio Del Bello, Yogita Farande, Mario Giannella, Maria Pigini, Giovanni Rafaiani, Antonio Carrieri, Consuelo Amantini, Roberta Lucciarini, Giorgio Santoni, Elena Poggesi & Amedeo Leonardi. (2008) Structure−Activity Relationships in 1,4-Benzodioxan-Related Compounds. 9. From 1,4-Benzodioxane to 1,4-Dioxane Ring as a Promising Template of Novel α 1D -Adrenoreceptor Antagonists, 5-HT 1A Full Agonists, and Cytotoxic Agents . Journal of Medicinal Chemistry 51:20, pages 6359-6370.
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Sarah A. Kavanagh, Alessandro Piccinini, Eimear M. Fleming & Stephen J. Connon. (2008) Urea derivatives are highly active catalysts for the base-mediated generation of terminal epoxides from aldehydes and trimethylsulfonium iodide. Organic & Biomolecular Chemistry 6:8, pages 1339.
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G. Dake. 2008. Comprehensive Heterocyclic Chemistry III. Comprehensive Heterocyclic Chemistry III 173 233 .
Gerhard Hilt, Patrick Bolze, Maja Heitbaum, Katrin Hasse, Klaus Harms & Werner Massa. (2007) Synthesis of Hexahydrocyclopenta[c]furans by an Intramolecular Iron-Catalyzed Ring Expansion Reaction. Advanced Synthesis & Catalysis 349:11-12, pages 2018-2026.
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John S. Ng, Chin Liu, Eoghan M. McGarrigle & Varinder K. Aggarwal. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
John S. Ng, Chin Liu, Eoghan M. McGarrigle & Varinder K. Aggarwal. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
Matej Sova, Andrej Babič, Slavko Pečar & Stanislav Gobec. (2007) Microwave-assisted synthesis of hydroxyethylamine dipeptide isosteres. Tetrahedron 63:1, pages 141-147.
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Henning Vogt, Thomas Baumann, Martin Nieger & Stefan Bräse. (2006) Direct Asymmetric α-Sulfamidation of α-Branched Aldehydes: A Novel Approach to Enamine Catalysis. European Journal of Organic Chemistry 2006:23, pages 5315-5338.
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David C. Forbes, Sejal R. Amin, Christie J. Bean & Michael C. Standen. (2006) Aryl-Substituted Sulfonium Betaines:  Preparation and Use in the Epoxidation of Aldehydes. The Journal of Organic Chemistry 71:21, pages 8287-8290.
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Hartmut Schirok. (2006) Microwave-Assisted Flexible Synthesis of 7-Azaindoles. The Journal of Organic Chemistry 71:15, pages 5538-5545.
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Andrej Babič, Matej Sova, Stanislav Gobec & Slavko Pečar. (2006) Epoxide opening with amino acids: improved synthesis of hydroxyethylamine dipeptide isosteres. Tetrahedron Letters 47:11, pages 1733-1735.
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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 .
Matthew Kwok Wai Choi & Patrick H Toy. (2004) Polymer-supported thioanisole: a versatile platform for organic synthesis reagents. Tetrahedron 60:12, pages 2875-2879.
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James A. Ciaccio, Antoinette L. Drahus, Regina M. Meis, Carice T. Tingle, Michael Smrtka & Richard Geneste. (2003) “Instant Methylide” Modification of the Corey—Chaykovsky Epoxide Synthesis.. ChemInform 34:43.
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