Planar Chiral Phosphoric Acids with Biphenylene-Tethered Paracyclophane Scaffolds: Synthesis, Characterization, and Catalytic Screening
| Autor: | Ivo Leito, Jean-François Betzer, Vincent Servajean, Julien Pastor, Angela Marinetti, Pascal Retailleau, Kévin Isaac, Gilles Frison, Karl Kaupmees, Jérémy Stemper |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire de chimie moléculaire (LCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), University of Tartu, Centre National de la Recherche Scientifique (CNRS), École polytechnique (X)-Centre National de la Recherche Scientifique (CNRS), Institute of Chemistry |
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
010405 organic chemistry
Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Enantioselective synthesis [CHIM.CATA]Chemical Sciences/Catalysis Biphenylene 010402 general chemistry 01 natural sciences 0104 chemical sciences Characterization (materials science) Catalysis [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry chemistry.chemical_compound Planar [CHIM]Chemical Sciences Organic chemistry Enantiomeric excess |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, American Chemical Society, 2014, 79 (20), pp.9639-9646. ⟨10.1021/jo501769t⟩ Journal of Organic Chemistry, American Chemical Society, 2014, 79, pp.9639-9646. ⟨10.1021/jo501769t⟩ |
| ISSN: | 0022-3263 1520-6904 |
| DOI: | 10.1021/jo501769t⟩ |
| Popis: | International audience; Phosphoric acids with planar chiral paracyclophane scaffolds have been prepared in optically pure form starting from 1,8-dibromobiphenylene, by means of a chiral phosphorodiamidate as the phosphorylating agent. Structural characterization and configurational assignment have been performed by X-ray diffraction studies. The acids promote the organocatalytic enantioselective H-transfer reduction of α-arylquinolines with up to 90% enantiomeric excess. |
| Databáze: | OpenAIRE |
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