117176-75-7Relevant academic research and scientific papers
An alternative synthesis of (8E,10Z)-tetradeca-8,10-dienal, sex pheromone of horse-chestnut leafminer (Cameraria ohridella)
Grodner, Jacek
, p. 1648 - 1654 (2009)
The stereoselective synthesis of the sex pheromone of horse-chestnut leafminer was efficiently carried out using methodology based on the Pd(0)-catalyzed cross-coupling of 1-pentynylmagnesium bromide with the corresponding vinyl iodides as the key step.
Copper-catalyzed asymmetric conjugate addition of trialkylaluminium reagents to trisubstituted enones: Construction of chiral quaternary centers
Vuagnoux-D'Augustin, Magali,Alexakis, Alexandre
, p. 9647 - 9662 (2008/12/21)
Me3Al, Et1Al, and vinylalane species undergo enantioselective conjugate addition to a wide range of 2- or 3-substituted enones (cyclopent-2enones, cyclohex-2-enones, 3-methyl cyclohept-2-enone) in the presence of catalytic amount of copper salt (copper thiophene carboxylate, [Cu(CH3-CN)4]BF4 or [CuOTf]2· C6H6) and tropos-phosphoramidite-based ligand. Thus, chiral quaternary centers can be built, with up to 98% ee after rigorous optimization of experimental conditions. It was shown that the main important parameter was the order of the introduction of the reagents. Then, the generated enantioenriched aluminium enolates and the chiral conjugate adducts were functionalized and used for subsequent reactions.
