Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids
| Autor: | Jérôme Désiré, Naresh Bhuma, Agnès Martin-Mingot, Jesús Jiménez-Barbero, Bastien Michelet, Yves Blériot, Zahra Abada, Aiichiro Nagaki, Sébastien Thibaudeau, Jérôme Marrot, Ludivine Lebedel, Ana Ardá, Masahiro Takumi, Hiroki Yamashita, Ali Abou-Hassan, Yutaka Shimizu |
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| Přispěvatelé: | Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), Institut national des sciences de l'Univers (INSU - CNRS)-Centre National de la Recherche Scientifique (CNRS)-Université de Poitiers-Institut de Chimie du CNRS (INC), Kyoto University [Kyoto], PHysicochimie des Electrolytes et Nanosystèmes InterfaciauX (PHENIX), Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Institut Lavoisier de Versailles (ILV), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
C glycosides Ferrier rearrangement Glycosylation [CHIM.ORGA]Chemical Sciences/Organic chemistry 010405 organic chemistry Glycoside Ionic bonding General Chemistry General Medicine 010402 general chemistry 01 natural sciences Catalysis Ion 0104 chemical sciences chemistry.chemical_compound chemistry Computational chemistry Glycosyl Superacid |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, 60 (4), pp.2036-2041. ⟨10.1002/anie.202010175⟩ |
| ISSN: | 1521-3757 0044-8249 1433-7851 1521-3773 |
| DOI: | 10.1002/ange.202010175 |
| Popis: | International audience; The transformation of glycals into 2,3-unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed to involve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experimentally. Herein, while combination of TfOH and flow conditions failed to observe this ionic species, its extended lifetime in superacid solutions allowed its characterization by NMRbased structural analysis, supported by DFT calculations. This allyloxycarbenium ion was further exploited in the Ferrier rearrangement to afford unsaturated nitrogen-containing C-aryl glycosides and C-alkyl glycosides under superacid and flow conditions respectively. |
| Databáze: | OpenAIRE |
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