STEREOSPECIFIC SYNTHESIS OF 1,5-DIEN-3-YNES AND 1,3,5-TRIENES. APPLICATION TO THE STEREOCHEMICAL IDENTIFICATION OF TRIENIC SEX PHEROMONES

Article abstract of DOI:10.1016/S0040-4020(01)81934-7

A one-pot sterospecific synthesis of 1,5-dien-3-ynes (Z) or (E) is described, based upon a palladium-catalyzed cross-coupling reaction between butenynylzinc bromide, generated in situ from 1,1-difluoroethylene, and an adequate iodoalkene.These dienynes are converted into the corresponding trienic compounds by (Z) semi-hydrogenation.