Stereoselective synthesis of enantiopure condensed [2.2]paracyclophanes |
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| Institution: | 1. Dipartimento di Chimica, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy;2. Central Institute for Chemistry, Hungarian Academy of Sciences, PO Box 17, 1525 Budapest, Hungary;1. Beckman Institute for Advanced Science and Technology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA;2. Chevron Phillips Chemical Company LP, Bartlesville, OK, 74004, USA;3. Departments of Bioengineering, Chemical and Biomolecular Engineering, Electrical and Computer Engineering, Mechanical Science and Engineering and Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA;1. Department of Chemistry and Technology of Polymers, Cracow University of Technology, Ul. Warszawska 24, 31-155, Krakow, Poland;2. Faculty of Chemistry, Maria Curie-Sk?odowska University, Plac Marii Curie-Sk?odowskiej 3, 20-031, Lublin, Poland;1. Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, China;2. Tsinghua-Peking Center for Life Sciences, Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China;3. School of Medicine, Tsinghua University, Beijing 100084, China;1. CCMAR and Department of Chemistry and Pharmacy, FCT, University of Algarve, Campus de Gambelas, Faro 8005-039, Portugal;2. CFisUC, Department of Physics, University of Coimbra, P-3004-516 Coimbra, Portugal;1. CNR-ISTEC, Institute of Science and Technology for Ceramics, Via Granarolo 64, I-48018 Faenza, Italy;2. CNR-ISM, Institute of Structure of Matter—Montelibretti Section, Via Salaria km 29.300, I-00015 Monterotondo Scalo, Italy;3. CNR-ISM, Institute of Structure of Matter—Tito Scalo Section, Zona Industriale, 85050 Tito Scalo (PZ), Italy;4. CNR-INO, National Institute of Optics, Largo E. Fermi, 6, I-50125 Firenze, Italy;1. College of Resources and Environment, Gansu Agricultural University, Lanzhou, Gansu 730070, PR China;2. College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, PR China |
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| Abstract: | The Diels–Alder reaction of (S)-(+)-4-ethenyl2.2]paracyclophane with 1,4-benzoquinone, N-phenylmaleimide and 3-nitrocyclohexen-1-one has been investigated under atmospheric and high pressure conditions. The synthesis of five optically active 2.2]paracyclophanes containing condensed polycyclic aromatic subunits is described. A structural analysis of the reaction products by 1H and 13C NMR spectroscopy is also presented. |
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