Continuous Flow Z-stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules
| Autor: | Duncan L. Browne, Marc Mauduit, Sophie Colombel-Rouen, Tom McBride, Jennifer Morvan, Thierry Roisnel, Idriss Curbet, Christophe Crévisy |
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| Přispěvatelé: | Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Cardiff University, University College of London [London] (UCL), This work was supported by the region Bretagne (ARED 2018 N° 601 – BIOMETA, grant to JM) and the FASO (grant to IC). TM thanks Cardiff University and EPSRC for a studentship (EP/N509449/1)., Umicore AG & Co is acknowledged for a generous gift of Ru-complexes. We are grateful to Elsa Caytan and the PRISM core facility (Biogenouest©, UMS, Biosit, Université de Rennes 1) for NMR experiences., Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA) |
| Rok vydání: | 2021 |
| Předmět: |
(Z)-Civetone
Olefin metathesis Chemistry Continuous flow 010405 organic chemistry Continuous reactor High selectivity Z-selectivity General Chemistry General Medicine 010402 general chemistry Combinatorial chemistry 01 natural sciences Catalysis Pheromones 0104 chemical sciences Sex pheromone Molecule continuous flow olefin metathesis [CHIM]Chemical Sciences Stereoselectivity |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie International Edition, 2021, 60 (36), pp.19685-19690. ⟨10.1002/anie.202106410⟩ Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, ⟨10.1002/anie.202106410⟩ |
| ISSN: | 1433-7851 1521-3773 |
| DOI: | 10.26434/chemrxiv.14579133 |
| Popis: | International audience; The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing- metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors. |
| Databáze: | OpenAIRE |
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