38363-24-5Relevant academic research and scientific papers
Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**
Browne, Duncan L.,Colombel-Rouen, Sophie,Crévisy, Christophe,Curbet, Idriss,Mauduit, Marc,McBride, Tom,Morvan, Jennifer,Roisnel, Thierry
supporting information, p. 19685 - 19690 (2021/08/06)
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.
A versatile and highly Z -Selective olefin metathesis ruthenium catalyst based on a readily accessible N -heterocyclic carbene
Dumas, Adrien,Tarrieu, Robert,Vives, Thomas,Roisnel, Thierry,Dorcet, Vincent,Baslé, Olivier,Mauduit, Marc
, p. 3257 - 3262 (2018/04/14)
A ruthenium catalyst for Z-selective olefin metathesis has been synthesized from a readily accessible N-heterocyclic carbene (NHC) ligand that is prepared using an efficient, practical, and scalable multicomponent synthesis. The desired ruthenium complex
Syntheses of Monounsaturated Sex Pheromones of Lepidoptera via 3-Alkyn-1-ols
Pop, Lidia,Oprean, I.,Barabas, A.,Hodosan, F.
, p. 867 - 878 (2007/10/02)
3-Alkyn-1-ols as intermediate synthons in the preparation of some Lepidoteran sex pheromones were utilized.Characteristic fragmentations reflecting the position of the triple bond were found in the mass spectra of 3-alkyn-1-ols and alkyn-1-yl acetates in contrast to 1-tert-butoxy-alkynes.A partial isomerization of 1-tosyloxy-3-(Z)-octene to 1-bromo-3-(E)-octene within the reaction with NaBr in DMF was noticed by GC and 13C-n.m.r., for which a mechanism involving homoconjugation in an intermediate non-classical carbonium ion was suggested.
