10.1002/chem.200903508
The research aims to develop a highly stereoselective synthesis method for imidazolidin-4-ones, which are important compounds with various biological activities and applications in peptidomimetics, chiral auxiliaries, and organocatalysts. The study introduces a three-component reaction based on a Br?nsted acid-catalyzed, remote-group-directed dynamic kinetic aza-Michael addition. Key chemicals used include pyridin-2-yl incorporated amino amides, aldehydes, and methyl vinyl ketone (MVK) as the Michael acceptor. The researchers optimized the reaction conditions, finding that trifluoroacetic acid (TFA) and isopropanol provided the best results. The method achieved excellent diastereoselectivity (d.r. >50:1) and good yields (up to 85%) for a range of substrates, including electron-poor and electron-rich aromatic aldehydes. The study concludes that this approach, which leverages a remote directing group and dynamic kinetic transformation, offers a convenient and stereoselective route to synthesize imidazolidin-4-ones, potentially applicable to other multicomponent reactions.
