Selective microwave-accelerated synthesis and polymerization of chiral methacrylamide directly from methacrylic acid and (R)-1-phenyl-ethylamine

The chiral (R)-N-(1-phenyl-ethyl)-methacrylamide was synthesized directly from methacrylic acid and (R)-1-phenyl-ethylamine through microwave irradiation in a solvent-free medium. Kinetic comparison between reactions carried out either under microwaves (MW) or conventional thermal heating evidenced the higher selectivity of the MW accelerated reaction. Under the MW applied conditions, the desired amidation is clearly preferred to the Michael side-reactions. The addition of a radical initiator to the starting mixture leads, in one step, to the formation of an optically active polymer containing both methacrylamide and imide moieties.