Morvan, J;
McBride, T;
Curbet, I;
Colombel-Rouen, S;
Roisnel, T;
Crévisy, C;
Browne, DL;
(2021)
Continuous Flow Z‐stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules.
Angewandte Chemie International Edition
, 133
(36)
pp. 19837-19842.
10.1002/anie.202106410.
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Abstract
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.
| Type: | Article |
|---|---|
| Title: | Continuous Flow Z‐stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/anie.202106410 |
| Publisher version: | https://doi.org/10.1002/anie.202106410 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| Keywords: | (Z)-Civetone, continuous flow, olefin metathesis, pheromones, Z-selectivity |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy UCL > Provost and Vice Provost Offices > School of Life and Medical Sciences > Faculty of Life Sciences > UCL School of Pharmacy > Pharma and Bio Chemistry |
| URI: | https://discovery-pp.ucl.ac.uk/id/eprint/10130573 |
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