An experimental investigation into the kinetics and mechanism of the aza-Michael additions of dimethyl itaconate

The aza-Michael addition is a versatile reaction for the modification of ?,?-unsaturated carbonyl compounds with amines. reactivity dimethyl itaconate as bio-based Michael acceptor explored in this work. Through its reactions piperidine and dibutylamine, it was found that order can be changed by choice catalyst, solvent, or concentration amine reactant. effectiveness catalysts proportional to their Lewis acidity. Competitive isomerisation into unreactive regioisomers suppressed using low-polarity solvents lower temperatures. This investigation additions has clarified possible mechanisms optimised protocol, supporting further use small molecule synthesis polymers.