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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 5
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Original Articles

Organic Base‐Catalyzed Stereoselective Isomerizations of 4‐Hydroxy‐4‐phenyl‐but‐2‐ynoic Acid Methyl Ester to (E)‐ and (Z)‐4‐Oxo‐4‐phenyl‐but‐2‐enoic Acid Methyl Esters

John P. Sonye Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, USA
&
Kazunori Koide Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania, USACorrespondence[email protected]
Pages 599-602 | Received 13 Apr 2005, Published online: 16 Aug 2006

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Masahiro Sai & Takatoki Mizuno. (2023) Potassium base-catalyzed redox isomerization of propargylic alcohols to chalcones. Synthetic Communications 53:3, pages 198-204.
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Articles from other publishers (18)

Chunmao Dong, Weiwei Peng, Huan Wang, Xiao Zhang, Jun Zhang, Guishan Tan, Kangping Xu, Zhenxing Zou & Haibo Tan. (2021) Total syntheses of melodienones by redox isomerization of propargylic alcohols. Organic & Biomolecular Chemistry 19:23, pages 5077-5081.
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Takafumi Yatabe, Noritaka Mizuno & Kazuya Yamaguchi. (2018) Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes. ACS Catalysis 8:12, pages 11564-11569.
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Bora Sieng, Matias Funes Maldonado, Carlo Romagnoli & Mohamed Amedjkouh. (2018) One‐Pot Alkynylation of Azaaryl Aldehydes and Spontaneous Base‐Free Rearrangement into Enone Esters: an Autoinductive Mechanism. European Journal of Organic Chemistry 2018:12, pages 1491-1495.
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E. Yu. Schmidt, I. A. Bidusenko, N. I. Protsuk, I. A. Ushakov, A. V. Ivanov, A. I. Mikhaleva & B. A. Trofimov. (2012) Features of the base-catalyzed reaction of 1-vinyl-4,5-dihydro-1H-benzo[g]indole-2-carbaldehyde with phenylacetylene. Chemistry of Heterocyclic Compounds 48:5, pages 822-824.
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M. Bhanuchandra, Malleswara Rao Kuram & Akhila K. Sahoo. (2012) A convenient approach to β-heteroarylated (C–N bond) ketones from Cs2CO3 promoted reaction between propargyl alcohols and nitrogen-heterocycles. Organic & Biomolecular Chemistry 10:17, pages 3538.
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Ya‐Hui Wang, Heng Liu, Li‐Li Zhu, Xiao‐Xiao Li & Zili Chen. (2011) Base‐Catalyzed Cascade 1,3‐H Shift/Cyclization Reaction to Construct Polyaromatic Furans. Advanced Synthesis & Catalysis 353:5, pages 707-712.
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Yohsuke Watanabe & Takashi Yamazaki. (2011) Application of Mitsunobu Reagents to Redox Isomerization of CF 3 -Containing Propargylic Alcohols to ( E )-α,β-Enones . The Journal of Organic Chemistry 76:6, pages 1957-1960.
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Victorio Cadierno, Pascale Crochet, Sergio E. García-Garrido & José Gimeno. (2010) Metal-catalyzed transformations of propargylic alcohols into α,β-unsaturated carbonyl compounds: from the Meyer–Schuster and Rupe rearrangements to redox isomerizations. Dalton Transactions 39:17, pages 4015.
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Ge Gao & Lin Pu. (2010) γ-Hydroxy-α,β-acetylenic esters: asymmetric syntheses and applications. Science China Chemistry 53:1, pages 21-35.
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Ramazan Erenler, Masaharu Uno, Thirumani Venkateshwar Goud & Jean-François Biellmann. (2009) Preparation of Some heterocyclic enones and ynones by isomerisation of the propargylic alcohols. Journal of Chemical Research 2009:7, pages 459-464.
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Yang Yue, Xiao‐Qi Yu & Lin Pu. (2009) Base‐Catalyzed Highly Stereoselective Conversion of γ‐Hydroxy‐α,β‐acetylenic Esters to γ‐Acetoxy Dienoates. Chemistry – A European Journal 15:20, pages 5104-5107.
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Sami Osman & Kazunori Koide. (2008) Cyclic acetal formation between 2-pyridinecarboxyaldehyde and γ-hydroxy-α,β-acetylenic esters. Tetrahedron Letters 49:46, pages 6550-6552.
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Hiroshi Naka, Daiki Koseki & Yoshinori Kondo. (2008) Catalytic Deprotonative Functionalization of Propargyl Silyl Ethers with Imines. Advanced Synthesis & Catalysis 350:11-12, pages 1901-1906.
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Brian J. Albert & Kazunori Koide. (2008) Zirconium-Promoted Epoxide Rearrangement−Alkynylation Sequence. The Journal of Organic Chemistry 73:3, pages 1093-1098.
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Xiaojun Han. (2007) A practical and expedient synthesis of 2-heterocycle (C–N bond) substituted 4-oxo-4-arylbutanoates. Tetrahedron Letters 48:16, pages 2845-2849.
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John P. Sonye & Kazunori Koide. (2007) Sodium Bicarbonate-Catalyzed Stereoselective Isomerizations of Electron-Deficient Propargylic Alcohols to ( Z )-Enones . The Journal of Organic Chemistry 72:5, pages 1846-1848.
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John P. Sonye & Kazunori Koide. (2006) Organic Base‐Catalyzed Stereoselective Isomerizations of 4‐Hydroxy‐4‐phenyl‐but‐2‐ynoic Acid Methyl Ester to (E)‐ and (Z)‐4‐Oxo‐4‐phenyl‐but‐2‐enoic Acid Methyl Esters.. ChemInform 37:34.
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John P. Sonye & Kazunori Koide. (2006) Base-Catalyzed Stereoselective Isomerization of Electron-Deficient Propargylic Alcohols to E -Enones . The Journal of Organic Chemistry 71:16, pages 6254-6257.
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