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Continuous flow Z-stereoselective Olefin Metathesis: development and applications in the synthesis of pheromones and macrocyclic odorant molecules

Morvan, Jennifer, McBride, Tom, Curbet, Idriss, Colombel-Rouen, Sophie, Roisnel, Thierry, Crévisy, Christophe, Browne, Duncan L. and Mauduit, Marc 2021. Continuous flow Z-stereoselective Olefin Metathesis: development and applications in the synthesis of pheromones and macrocyclic odorant molecules. Angewandte Chemie International Edition 60 (36) , pp. 19685-19690. 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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Wiley
ISSN: 1521-3773
Funders: EPSRC
Date of First Compliant Deposit: 5 November 2021
Date of Acceptance: 29 June 2021
Last Modified: 30 Jun 2022 02:03
URI: https://orca.cardiff.ac.uk/id/eprint/145313

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