Ethylaluminum Dichloride Catalyzed Ene Reactions of Aldehydes with Nonnucleophilic Alkenes

Article abstract of DOI:10.1021/jo00152a011

Ethylaluminum dichloride, which is a strong Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic aldehydes with nonnucleophilic alkenes.Higher aldehydes give good yields of ene adducts with terminal alkenes.Formaldehyde gives good yields of adducts with electron-deficient alkenes.This reaction has been used for the synthesis of recifeiolide, ricinelaidic acid, and the insect pheromones (E,E)-8,10-dodecadienyl acetate and (E)-9,11-dodecadienyl acetate.