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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 9
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Original Articles

Conversion of 1,3-Dicarbonyls to 1,4-Dicarbonyls

Kazuhiko Saigo Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan
,
Hiroshi Kurihara Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan; Department of Applied Chemistry, Faculty of Engineering, Saitama University, Shimo-ohkubo, Urawa, 338, Japan
,
Hisao Miura Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan; Department of Applied Chemistry, Faculty of Engineering, Saitama University, Shimo-ohkubo, Urawa, 338, Japan
,
Akinori Hongu Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan
,
Naomi Kubota Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan
,
Hiroyuki Nohira Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan; Department of Applied Chemistry, Faculty of Engineering, Saitama University, Shimo-ohkubo, Urawa, 338, Japan
&
Masaki Hasegawa Department of Synthetic Chemistry, Faculty of Engineering, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113, Japan
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Pages 787-796 | Published online: 19 Dec 2006

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Tetsuo Miyakoshi. (1989) PREPARATION AND REACTIONS OF 4-OXOCARBONYL COMPOUNDS. A REVIEW. Organic Preparations and Procedures International 21:6, pages 659-704.
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Kazuhiko Saigo, Takashi Yamashita, Akinori Hongu & Masaki Hasegawa. (1985) The Double Simmons-Smith Reactions VIA Silatropies. Synthetic Communications 15:8, pages 715-721.
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Articles from other publishers (28)

Zeynep Dilşad Susam, Merve Bozdemir, Gülsüm Gündoğdu & Cihangir Tanyeli. (2022) Enantioselective synthesis of 2,3-dihydrofurans using a bifunctional quinine/squaramide organocatalyst. New Journal of Chemistry 46:2, pages 599-606.
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Rafael D. C. Gallo, Marcelo Duarte, Amanda F. da Silva, Celso Y. OkadaJr.Jr., Victor M. Deflon & Igor D. Jurberg. (2021) A Selective C–C Bond Cleavage Strategy Promoted by Visible Light. Organic Letters 23:22, pages 8916-8920.
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Zhaohong Liu, Paramasivam Sivaguru, Giuseppe Zanoni, Edward A. Anderson & Xihe Bi. (2018) Catalyst‐Dependent Chemoselective Formal Insertion of Diazo Compounds into C−C or C−H Bonds of 1,3‐Dicarbonyl Compounds. Angewandte Chemie International Edition 57:29, pages 8927-8931.
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Zhaohong Liu, Paramasivam Sivaguru, Giuseppe Zanoni, Edward A. Anderson & Xihe Bi. (2018) Catalyst‐Dependent Chemoselective Formal Insertion of Diazo Compounds into C−C or C−H Bonds of 1,3‐Dicarbonyl Compounds. Angewandte Chemie 130:29, pages 9065-9069.
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K. Rybicka‐Jasińska, Ł. W. Ciszewski & D. Gryko. (2016) Photocatalytic Reaction of Diazo Compounds with Aldehydes. Advanced Synthesis & Catalysis 358:10, pages 1671-1678.
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Juhua Feng, Lili Lin, Kunru Yu, Xiaohua Liu & Xiaoming Feng. (2015) Asymmetric Synthesis of Dihydrofurans via Organocatalytic Domino Michael–Alkylation Reaction. Advanced Synthesis & Catalysis 357:6, pages 1305-1310.
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Jian-Wu Xie, Ping Li, Ting Wang & Fei-Ting Zhou. (2011) Efficient and mild synthesis of functionalized 2,3-dihydrofuran derivatives via domino reaction in water. Tetrahedron Letters 52:18, pages 2379-2382.
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Wilhelm A. Eger, Charles K. Zercher & Craig M. Williams. (2010) A Mechanistic Investigation into the Zinc Carbenoid-Mediated Homologation Reaction by DFT Methods: Is a Classical Donor−Acceptor Cyclopropane Intermediate Involved?. The Journal of Organic Chemistry 75:21, pages 7322-7331.
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Hai‐Yan JIANG, Wei‐Guo CAO, Hui ZHANG, Ru‐Shu SUN, Jie CHEN, Hong‐Mei DENG, Min SHAO & Shi‐Zheng ZHU. (2008) Stereoselective Synthesis of trans ‐2‐Thien‐ α ‐oyl‐3‐ [(un)substituted phenyl]‐4‐acetyl‐5‐methyl‐2,3‐dihydrofurans . Chinese Journal of Chemistry 26:4, pages 736-740.
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Hui Zhang, Wei‐Guo Cao, Jie Chen, Ji‐Rong Hu, Jia‐Xian Qian & Shi‐Zheng Zhu. (2007) Highly Stereoselective Synthesis of trans ‐3‐Aryl‐4‐carbethoxy‐2,3‐dihydro‐2‐fur‐2′‐oyl‐5‐methylfurans . Chinese Journal of Chemistry 25:7, pages 968-972.
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Guoren Yue, Xuegong She, Zheng Zhang & Xinfu Pan. (2019) A Tandem Michael Addition–Rearrangement–Carbonylation by (4-Nitrophenylsulfonylmethyl) Benzene and Its Derivatives with Methacrylates under PTC. Journal of Chemical Research 2003:9, pages 559-561.
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Oleg G. Kulinkovich. (2003) The Chemistry of Cyclopropanols. Chemical Reviews 103:7, pages 2597-2632.
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Matthew D. Ronsheim, Ramona K. Hilgenkamp & Charles K. Zercher. 2003. Organic Syntheses. Organic Syntheses 146 146 .
Ramona Hilgenkamp & Charles K Zercher. (2001) Zinc carbenoid-mediated chain extension of β-keto amides. Tetrahedron 57:42, pages 8793-8800.
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Ramona Hilgenkamp & Charles K. Zercher. (2001) Tandem Chain Extension-Homoenolate Formation:  The Formation of α-Methylated-γ-Keto Esters. Organic Letters 3:19, pages 3037-3040.
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Huw M. L. Davies & Evan G. Antoulinakis. 2004. Organic Reactions. Organic Reactions 1 326 .
Osamu Okitsu, Ritsu Suzuki & Shū Kobayashi. (2001) Efficient Synthesis of Piperidine Derivatives. Development of Metal Triflate-Catalyzed Diastereoselective Nucleophilic Substitution Reactions of 2-Methoxy- and 2-Acyloxypiperidines. The Journal of Organic Chemistry 66:3, pages 809-823.
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John B. Brogan & Charles K. Zercher. (1997) Zinc-Mediated Conversion of β-Keto Esters to γ-Keto Esters. The Journal of Organic Chemistry 62:18, pages 6444-6446.
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Minoru Hayashi & Kazuhiko Saigo. (1997) Palladium-Catalyzed Regioselective Bis-Alkynylation of Propargylic Carbonates: Synthesis of Enediyne Compounds. Tetrahedron Letters 38:35, pages 6241-6244.
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Albert Padwa & David J. Austin. (2003) Ligand Effects on the Chemoselectivity of Transition Metal Catalyzed Reactions of α‐Diazo Carbonyl Compounds. Angewandte Chemie International Edition in English 33:18, pages 1797-1815.
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Albert Padwa & David J. Austin. (2006) Übergangsmetallkatalysierte Reaktionen von α‐Diazocarbonylverbindungen – Einfluß der Liganden auf die Chemoselektivität. Angewandte Chemie 106:18, pages 1881-1899.
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Huw M.L. Davies. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 1031 1067 .
Marcel Gaudemar & Moncef Bellassoued. (1989) Regio and stereoselective preparation of enolates from ketones by means of sodium bis(trimethylsilyl)-azide. Tetrahedron Letters 30:21, pages 2779-2782.
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A. Arcadi, S. Cacchi, F. Marinelli & D. Misiti. (1988) The reaction of alkyl 4-hydroxy-2-alkynoates and 4-hydroxy-2-alkyn-1-ones with palladium tributylammonium formate and with tributylamine: Preparation of 1,4-dicarbonyl compounds. Tetrahedron Letters 29:12, pages 1457-1460.
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M. S. Baird, H.-U. Reißig & J. R. Y. SalaünHans-Ulrich Reißig. 1988. Small ring compounds in organic synthesis III. Small ring compounds in organic synthesis III 73 135 .
Gerhard Maas. 1987. Organic Synthesis, Reactions and Mechanisms. Organic Synthesis, Reactions and Mechanisms 75 253 .
K. SAIGO, H. KURIHARA, H. MIURA, A. HONGU, N. KUBOTA, H. NOHIRA & M. HASEGAWA. (2016) ChemInform Abstract: CONVERSION OF 1,3‐DICARBONYLS TO 1,4‐DICARBONYLS. Chemischer Informationsdienst 16:5.
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