A Method To Accomplish a 1,4-Addition Reaction of Bulky Nucleophiles to Enones and Subsequent Formation of Reactive Enolates

[reaction: see text] BF(3)-promoted 1,4-addition of bulky aryl groups to alpha-iodo enones, prepared from the parent enones, afforded beta-aryl-alpha-iodo ketones. Subsequent reaction with EtMgBr furnished the magnesium enolates, which upon reactions with ClP(O)(OEt)(2) and aldehydes gave enol phosphates and aldols, respectively. This method was applied successfully to a synthesis of Delta(1)-trans-tetrahydrocannabinol.