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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 35, 2005 - Issue 5

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Original Articles

Anodic Cyanation of (−)‐N‐Phenyl‐2‐Methylpiperidine: A Short Synthesis of (+)‐Solenopsin A and (+)‐Isosolenopsin A

Nicolas Girard Laboratoire d'électrochimie, UMR 6509, Institut de Chimie, Université de Rennes I, Rennes Cedex, France

Jean‐Pierre Hurvois Laboratoire d'électrochimie, UMR 6509, Institut de Chimie, Université de Rennes I, Rennes Cedex, FranceCorrespondence[email protected]

Loic Toupet Groupe Matière Condensée et Matériaux, Université de Rennes I, Rennes Cedex, France

Claude Moinet Laboratoire d'électrochimie, UMR 6509, Institut de Chimie, Université de Rennes I, Rennes Cedex, France

Pages 711-723 | Published online: 20 Aug 2006

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https://doi.org/10.1081/SCC-200050370

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Majid M. Heravi, Neda Abedian‐Dehaghani, Vahideh Zadsirjan & Yalda Rangraz. (2021) Catalytic Function of Cu (I) and Cu (II) in Total Synthesis of Alkaloids. ChemistrySelect 6:34, pages 9230-9287.
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Majid M. Heravi & Vahideh Zadsirjan. 2021. Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids. Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids 153 190 .

Heesun Yu, Hyoungsu Kim, Seung-Hoon Baek & Dongjoo Lee. (2020) Direct and Efficient C(sp3)–H Functionalization of N-Acyl/Sulfonyl Tetrahydroisoquinolines (THIQs) With Electron-Rich Nucleophiles via 2,3-Dichloro-5,6-Dicyano-1,4-Benzoquinone (DDQ) Oxidation. Frontiers in Chemistry 8.
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Wei Ou, Guang-Sheng Lu, Dong An, Feng Han & Pei-Qiang Huang. (2020) Two-Step Catalytic Transformation of N -Benzyllactams to Alkaloids (±)-Solenopsin, (±)-Solenopsin A, and (+)-Julifloridine . European Journal of Organic Chemistry 2020:1, pages 52-56.
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Hong Kim, Heesun Yu, Hyoungsu Kim, Seok-Ho Kim & Dongjoo Lee. (2018) DDQ-Promoted Mild and Efficient Metal-Free Oxidative α-Cyanation of N-Acyl/Sulfonyl 1,2,3,4-Tetrahydroisoquinolines. Molecules 23:12, pages 3223.
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Birgit Gröll, Patricia Schaaf & Michael Schnürch. (2016) Improved simplicity and practicability in copper-catalyzed alkynylation of tetrahydroisoquinoline. Monatshefte für Chemie - Chemical Monthly 148:1, pages 91-104.
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Jing-Bo Yu, Gang Peng, Zhi-Jiang Jiang, Zi-Kun Hong & Wei-Ke Su. (2016) Mechanochemical Oxidative Mannich Reaction: Evaluation of Chemical and Mechanical Parameters for the Mild and Chemoselective Coupling of N - tert -butoxycarbonyltetrahydroquinolines and Ketones . European Journal of Organic Chemistry 2016:32, pages 5340-5344.
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Changcun Yan, Lili Li, Yuxiu Liu & Qingmin Wang. (2016) Direct and Oxidant-Free Electron-Deficient Arylation of N -Acyl-Protected Tetrahydroisoquinolines . Organic Letters 18:18, pages 4686-4689.
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Yi Sun, Gang Wang, Jiayu Chen, Chang Liu, Manqi Cai, Rongxiu Zhu, Haofei Huang, Wei Li & Lei Liu. (2016) A practical oxidative C–H functionalization of N-carbamoyl tetrahydro-β-carbolines with diverse potassium trifluoroborates. Organic & Biomolecular Chemistry 14:39, pages 9431-9438.
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Changcun Yan, Yuxiu Liu & Qingmin Wang. (2015) Direct C–H Allylation of N -Acyl/Sulfonyl Tetrahydroisoquinolines and Analogues . Organic Letters 17:22, pages 5714-5717.
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H. Surya Prakash Rao & Elamvazhuthi Poonguzhali. (2015) Synthesis and stereochemistry of cis-2,6-diphenyl-1-alkylpiperidines. Tetrahedron Letters 56:45, pages 6190-6193.
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Y. Sheena Mary, Hema Tresa Varghese, C. Yohannan Panicker, M. Girisha, B.K. Sagar, H.S. Yathirajan, Abdulaziz A. Al-Saadi & Christian Van Alsenoy. (2015) Vibrational spectra, HOMO, LUMO, NBO, MEP analysis and molecular docking study of 2,2-diphenyl-4-(piperidin-1-yl)butanamide. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 150, pages 543-556.
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C. Yohannan Panicker, Hema Tresa Varghese, Prakash S. Nayak, B. Narayana, B.K. Sarojini, H.K. Fun, Javeed Ahamad War, S.K. Srivastava & C. Van Alsenoy. (2015) Infrared spectrum, NBO, HOMO–LUMO, MEP and molecular docking studies (2E)-3-(3-nitrophenyl)-1-[4-piperidin-1-yl]prop-2-en-1-one. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 148, pages 18-28.
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Yang Yang. (2015) Building polyfunctional piperidines: a stereoselective strategy of a three-component Mannich reaction inspired by biosynthesis and applications in the synthesis of natural alkaloids (+)-241D; (−)-241D; isosolenopsin A and (−)-epimyrtine. RSC Advances 5:24, pages 18894-18908.
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Henri Brunner, Takashi Tsuno, Gábor Balázs & Michael Bodensteiner. (2014) Methyl/Phenyl Attraction by CH/π Interaction in 1,2-Substitution Patterns. The Journal of Organic Chemistry 79:23, pages 11454-11462.
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Nicola Otto & Till Opatz. (2014) Heterocycles from α‐Aminonitriles. Chemistry – A European Journal 20:41, pages 13064-13077.
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Zhiyu Xie, Lei Liu, Wenfang Chen, Hongbo Zheng, Qingqing Xu, Huiqing Yuan & Hongxiang Lou. (2014) Practical Metal‐Free C(sp 3 )H Functionalization: Construction of Structurally Diverse α‐Substituted N ‐Benzyl and N ‐Allyl Carbamates . Angewandte Chemie International Edition 53:15, pages 3904-3908.
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Wenfang Chen, Hongbo Zheng, Xinhui Pan, Zhiyu Xie, Xin Zan, Bin Sun, Lei Liu & Hongxiang Lou. (2014) A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate. Tetrahedron Letters 55:17, pages 2879-2882.
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G. Velraj, S. Soundharam & C. Sridevi. (2014) Structure, vibrational, electronic, NBO and NMR analyses of 3-methyl-2,6-diphenylpiperidin-4-one (MDPO) by experimental and theoretical approach. Journal of Molecular Structure 1060, pages 156-165.
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Xigong Liu, Bin Sun, Zhiyu Xie, Xiaojun Qin, Lei Liu & Hongxiang Lou. (2013) Manganese Dioxide–Methanesulfonic Acid Promoted Direct Dehydrogenative Alkylation of sp 3 C–H Bonds Adjacent to a Heteroatom . The Journal of Organic Chemistry 78:7, pages 3104-3112.
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Isabelle Abrunhosa-Thomas, Aurélie Plas, Alexandre Vogrig, Nishanth Kandepedu, Pierre Chalard & Yves Troin. (2013) Access to 2,6-Disubstituted Piperidines: Control of the Diastereoselectivity, Scope, and Limitations. Applications to the Stereoselective Synthesis of (−)-Solenopsine A and Alkaloid (+)-241D. The Journal of Organic Chemistry 78:6, pages 2511-2526.
Crossref

Adriana Pianaro, Eduardo G.P. Fox, Odair C. Bueno & Anita J. Marsaioli. (2012) Rapid configuration analysis of the solenopsins. Tetrahedron: Asymmetry 23:9, pages 635-642.
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Michael Ghobrial, Michael Schnürch & Marko D. Mihovilovic. (2011) Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms. The Journal of Organic Chemistry 76:21, pages 8781-8793.
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Michael Ghobrial, Karin Harhammer, Marko D. Mihovilovic & Michael Schnürch. (2010) Facile, solvent and ligand free iron catalyzed direct functionalization of N-protected tetrahydroisoquinolines and isochroman. Chemical Communications 46:46, pages 8836.
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Karin Leijondahl, Linnéa Borén, Roland Braun & Jan-E. Bäckvall. (2009) Enzyme- and Ruthenium-Catalyzed Dynamic Kinetic Asymmetric Transformation of 1,5-Diols. Application to the Synthesis of (+)-Solenopsin A. The Journal of Organic Chemistry 74:5, pages 1988-1993.
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Jeanne L. Bolliger & Christian M. Frech. (2009) Transition metal-free amination of aryl halides—A simple and reliable method for the efficient and high-yielding synthesis of N-arylated amines. Tetrahedron 65:6, pages 1180-1187.
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Franklin A. Davis, He Xu & Junyi Zhang. (2007) Asymmetric Synthesis of Ring Functionalized trans -2,6-Disubstituted Piperidines from N -Sulfinyl δ-Amino β-Keto Phosphonates. Total Synthesis of (−)-Myrtine . The Journal of Organic Chemistry 72:6, pages 2046-2052.
Crossref

Nicolas Girard, Jean‐Pierre Hurvois, Loic Toupet & Claude Moinet. (2005) Anodic Cyanation of (‐)‐N‐Phenyl‐2‐methylpiperidine: A Short Synthesis of (+)‐Solenopsin A and (+)‐Isosolenopsin A.. ChemInform 36:48.
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Anodic Cyanation of (−)‐N‐Phenyl‐2‐Methylpiperidine: A Short Synthesis of (+)‐Solenopsin A and (+)‐Isosolenopsin A

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Anodic Cyanation of (−)‐N‐Phenyl‐2‐Methylpiperidine: A Short Synthesis of (+)‐Solenopsin A and (+)‐Isosolenopsin A

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