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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 35, 2005 - Issue 1
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Original Articles

Cycloisomerization of Olefinic Carboxylic Acids Catalyzed by Trifluoromethanesulfonic Acid

Lydie Coulombel Laboratoire Arômes, Synthèses et Interactions, UMR CNRS 6001 Université de Nice‐Sophia Antipolis, Parc Valrose, Nice cedex 2, France
&
Elisabet Duñach Laboratoire de Chimie Bio‐Organique, UMR CNRS 6001 Université de Nice‐Sophia Antipolis, Parc Valrose, 06108, Nice cedex 2, France; Laboratoire Arômes, Synthèses et Interactions, UMR CNRS 6001 Université de Nice‐Sophia Antipolis, Parc Valrose, Nice cedex 2, FranceCorrespondence[email protected]
Pages 153-160 | Received 19 Sep 2004, Published online: 22 Jun 2006

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Shijie Du, Mingan Wang, Wen Zhu & Zhaohai Qin. (2009) A new fungicidal lactone from Xylocarpus granatum (Meliaceae). Natural Product Research 23:14, pages 1316-1321.
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Articles from other publishers (27)

Yibing Liu, Liqun Hu, Yuzhu Zheng, Xiong Fang & Youwei Xie. (2022) Re 2 O 7 /HReO 4 Mediated Intramolecular Hydroacyloxylation of Unactivated Alkenes: A Dual Hydrogen-Bonding Effect . Organic Letters 25:1, pages 64-69.
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Xuyang Yan, Bangkui Yu, Haocheng Zhang & Hanmin Huang. (2022) Copper-Catalyzed Claisen Rearrangement with AIBN and Allylic Alcohols. The Journal of Organic Chemistry 87:24, pages 16918-16927.
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Hailong Zhang, Romain Carlino, Régis Guillot, Richard Gil, Sophie Bezzenine & Jérôme Hannedouche. (2022) Substrate-Dependent Selectivity in Sc(OTf)3-Catalyzed Cyclization of Alkenoic Acids and N-Protected Alkenamides. Catalysts 12:11, pages 1481.
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Sergey B. Alyabyev & Irina P. Beletskaya. (2020) Gold as a catalyst. Part III. Addition to double bonds. Russian Chemical Reviews 89:5, pages 491-536.
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Chenxiao Qi, Shengwen Yang, Vincent Gandon & David Lebœuf. (2019) Calcium(II)- and Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol. Organic Letters 21:18, pages 7405-7409.
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Zhong-Yu Xie, Jin Deng & Yao Fu. (2018) W(OTf) 6 -Catalyzed Synthesis of γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid . ChemSusChem 11:14, pages 2332-2339.
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Richard C. LarockRichard C. Larock & Roman Rozhkov. 2018. Comprehensive Organic Transformations. Comprehensive Organic Transformations 1 102 .
Irina Geibel, Anna Dierks, Thomas Müller & Jens Christoffers. (2017) Formation of δ‐Lactones with anti ‐Baeyer–Villiger Regiochemistry: Investigations into the Mechanism of the Cerium‐Catalyzed Aerobic Coupling of β‐Oxoesters with Enol Acetates . Chemistry – A European Journal 23:30, pages 7245-7254.
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Kazuaki Ishihara. 2016. From Biosynthesis to Total Synthesis. From Biosynthesis to Total Synthesis 296 330 .
Nayyar Ahmad Aslam & Srinivasarao Arulananda Babu. (2014) Direct lactonization of α-amino γ,δ-unsaturated carboxylic acid esters via olefin activation: stereo- and regioselective production of homoserine lactone scaffolds having contiguous stereocenters. Tetrahedron 70:37, pages 6402-6419.
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Masayuki Sakuma, Akira Sakakura & Kazuaki Ishihara. (2013) Kinetic Resolution of Racemic Carboxylic Acids through Asymmetric Protolactonization Promoted by Chiral Phosphonous Acid Diester. Organic Letters 15:11, pages 2838-2841.
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Gilles Lemière & Elisabet Duñach. (2013) Catalytic Activation of Olefins by Metal Triflates and Triflimides: Application to Fragrance Chemistry. Chemistry – A European Journal 19:10, pages 3270-3280.
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Jean‐François Gal, Claudio Iacobucci, Ilaria Monfardini, Lionel Massi, Elisabet Duñach & Sandra Olivero. (2012) Metal triflates and triflimides as Lewis “superacids”: preparation, synthetic application and affinity tests by mass spectrometry. Journal of Physical Organic Chemistry 26:2, pages 87-97.
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Elena M. Barreiro, Luis A. Adrio, King Kuok (Mimi) Hii & John B. Brazier. (2013) Coinage Metal Catalysts for the Addition of O–H to C=C Bonds. European Journal of Organic Chemistry 2013:6, pages 1027-1039.
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Christian Chapuis. (2012) The Jubilee of Methyl Jasmonate and Hedione ® . Helvetica Chimica Acta 95:9, pages 1479-1511.
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Rachel E. McKinney Brooner & Ross A. Widenhoefer. (2011) Stereochemistry and Mechanism of the Brønsted Acid Catalyzed Intramolecular Hydrofunctionalization of an Unactivated Cyclic Alkene. Chemistry – A European Journal 17:22, pages 6170-6178.
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Luis A. Adrio & King Kuok (Mimi) Hii. (2011) An Expedient Synthesis of Olfactory Lactones by Intramolecular Hydroacylalkoxylation Reactions. European Journal of Organic Chemistry 2011:10, pages 1852-1857.
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Lukas J. Gooßen, Dominik M. Ohlmann & Markus Dierker. (2010) Silver triflate-catalysed synthesis of γ-lactones from fatty acids. Green Chem. 12:2, pages 197-200.
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Luis A. Adrio, Louisa Shuyi Quek, Jason G. Taylor & King Kuok (Mimi) Hii. (2009) Copper-catalysed intramolecular O–H addition to unactivated alkenes. Tetrahedron 65:50, pages 10334-10338.
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M. Paz Muñoz & Guy C. Lloyd‐Jones. (2009) Triflic Acid Mediated Dealkylative Lactonisation via NMR‐Observable Alkyloxonium Intermediates. European Journal of Organic Chemistry 2009:4, pages 516-524.
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George A. Olah, G. K. Surya Prakash, Árpád Molnár & Jean Sommer. 2009. Superacid Chemistry. Superacid Chemistry 501 788 .
V. N. Emel’yanenko, S. P. Verevkin, E. N. Burakova, G. N. Roganov & M. K. Georgieva. (2009) The thermodynamic properties of delta-lactones. Russian Journal of Physical Chemistry A 83:8, pages 1271-1279.
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Carmen Martín, Tomás R. Belderraín & Pedro J. Pérez. (2009) Rediscovering copper-based catalysts for intramolecular carbon–hydrogen bond functionalization by carbene insertion. Organic & Biomolecular Chemistry 7:22, pages 4777.
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Lydie Coulombel, Fanny Grau, Michel Weïwer, Isabelle Favier, Xavier Chaminade, Andreas Heumann, J. Carles Bayón, Pedro A. Aguirre & Elisabet Duñach. (2008) Lewis Super‐Acid Catalyzed Cyclizations: A New Route to Fragrance Compounds . Chemistry & Biodiversity 5:6, pages 1070-1082.
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Yuying Du & Fuli Tian. (2007) Efficient synthesis of 1,3-dioxanes catalyzed by trifluoromethanesulfonic acid using formalin as formaldehyde source. Catalysis Communications 8:12, pages 2012-2016.
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Yibo Zhou, L. Keith Woo & Robert J. Angelici. (2007) Solid acid catalysis of tandem isomerization-lactonization of olefinic acids. Applied Catalysis A: General 333:2, pages 238-244.
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Lydie Coulombel & Elisabet Dunach. (2005) Cycloisomerization of Olefinic Carboxylic Acids Catalyzed by Trifluoromethanesulfonic Acid.. ChemInform 36:27.
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