115. Asymmetric additions of 1-alkenylcopper reagents to chiral enoates: Enantioselective synthesis of california red scale pheromone.
     Oppolzer, W.; Stevenson, T.
     Tetrahedron Lett. 1986, 27, 1139-1140

nBu₃P-stabilized 1-alkenylcopper reagents undergo efficient 1,4-additions to enoates 1 and 5. Thus, acids 3, 7 or alcohols 4, 8 were obtained in high e.e. with recovery of the auxiliary. 4d was converted to pure (-)-pheromone 13, and 8b gave bromide 14b.

DOI : 10.1016/S0040-4039(00)84198-2