Direct organocatalytic in situ generation of novel push–pull dienamines: application in tandem Claisen–Schmidt/iso-aromatization reactions

A new, green, regioselective, one-step, tandem reaction of an aldehyde possessing a non-enolizable carbonyl function with a highly substituted cyclohex-2-enone, under amine catalysis afforded highly substituted phenols or 2-arylidenecyclohexanones, respectively. The yields and regioselectivities were good. Evidence for a pathway involving formation of novel push–pull dienamines is presented along with examples demonstrating the amenability of the process to combinatorial chemistry.