ASYMMETRIC ADDITION OF 1-ALKENYLCOPPER REAGENTS TO CHIRAL ENOATES: ENANTIOSELECTIVE SYNTHESIS OF CALIFORNIA RED SCALE PHEROMONE.

Article abstract of DOI:10.1016/S0040-4039(00)84198-2

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.