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

摘要

BF_3-promoted 1, 4-addition of bulky aryl groups to #alpha#-iodo enones, prepared from the parnet enones, afforded #beta#-aryl-#alpha#-iodo ketones. Subsequent reaction with EtMgBr furnished the magnesium enolates, which upon reactions with CIP(O)(OEt)_2 and aldehydes gave enol phosphates and aldols, respectively. This method was applied successfully to a synthesis of (triangl open)~1-trans-tertrahydrocannabinol.