Palladium-catalyzed carboamination reactions for the synthesis of imidazolidin-2-ones and related heterocycles

Imidazolidin-2-ones and related heterocycles have many medicinal and synthetic uses. Progress toward expanding the scope of Pd-catalyzed carboamination to include the synthesis of these classes of heterocycles is demonstrated. 4,4- and 4,5-disubstituted imidazolidin-2-ones were generated in high yield from N-allylureas and aryl bromides. 4,5-disubstituted imidazolidin-2-ones and imidazolidin-2-ones derived from internal olefins were made in moderate to high diastereoselectivity. Vinyl halides were also shown to be effective coupling partners. Orthoganol deprotection of an N1-benzyl N3 p-methoxyphenyl protected imidazolidin-2-ones was achieved. An enantioselective synthesis of imidazolidin-2-ones using chiral ligands or chiral auxiliaries was pursued. Lastly, studies on the Pd-catalyzed carboamination of N-allylguanidines, O -allylcarbamate, homoallylsulfoximines, and N-allylsulfamides are described.