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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:

L. Fernandes, A. J. Bortoluzzi, M. M. Sa, Tetrahedron, 2004, 60, 9983-9989.

DOI: 10.1016/j.tet.2004.08.018


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.

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Key Words

Insect pheromones, Trisubstituted olefins, 2-Methylalkenoates, Allyl Bromides, α,β-Unsaturated Esters, Dehalogenation, Zinc, Reduction

ID: J72-Y2004-910