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Continuous Flow Z ‐Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules **
Author(s) -
Morvan Jennifer,
McBride Tom,
Curbet Idriss,
ColombelRouen Sophie,
Roisnel Thierry,
Crévisy Christophe,
Browne Duncan L.,
Mauduit Marc
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202106410
Subject(s) - stereoselectivity , continuous flow , olefin metathesis , metathesis , olefin fiber , chemistry , sex pheromone , stereochemistry , catalysis , organic chemistry , botany , biology , biochemical engineering , engineering , polymer , polymerization
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.