Simple access to 2-methylalk-2-enoates and insect pheromones by zinc-promoted reduction of Baylis–Hillman-derived allylic bromides
Luciano Fernandes, Adailton J. Bortoluzzi and Marcus M. Sá*
*Departamento de Química, Universidade Federal de Santa Catarina,
Florianópolis, SC 88040-900, Brazil, Email: msa
qmc.ufsc.br
L. Fernandes, A. J. Bortoluzzi, M. M. Sa, Tetrahedron, 2004, 60, 9983-9989.
DOI: 10.1016/j.tet.2004.08.018
Abstract
Zinc-promoted reduction of 2-(bromomethyl)alkenoates derived from Baylis–Hillman adducts gave (E)-2-methylacrylates in good yield and high stereoselectivity. Synthesis of the male ant pheromone (E)-2,4-dimethyl-2-hexenoic acid was performed using this simple methodology.
see article for more reactions
Zusammenfassung
Zink-induzierte Reduktion von 2-(Bromomethyl)alkenoaten hergestellt aus Baylis-Hillman-Addukten ergab (E)-2-Methylacrylate in guten Ausbeuten und mit sehr guter Stereoselektivität. Die Synthese des Pheromones (E)-2,4-Dimethyl-2-hexensäure der männlichen Ameise wurde nach dieser Methodik durchgeführt.
Key Words
Insect pheromones, Baylis–Hillman, Trisubstituted olefins, 2-Methylalkenoates, Reduction
Schlüsselworte
Insekten-Pheromone, Baylis-Hillman, dreifach-substituierte Olefine, 2-Methylalkenoate, Reduktion
ID: J72-Y2004-910
