Intramolecular N-Carbamoyliminium Ion Cyclizations of Unactivated Alkenes and Acetylenes

Article abstract of DOI:10.1021/jo00194a027

A select series of 3-alkenyl (7a-e) and 3-acetylenic (7f) 4-hydroxy-5,5-dimethylimidazolidin-2-ones were prepared.Treatment of each substrate except 7e with acid led to the desired intramolecular amidoalkylation reaction to give the bicyclic imidazolidin-2-ones.The reactions proceeded regio- and stereoselectively in moderate to good yields.The mechanism of these and related transformations are discussed.