title: Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones.
abstract: Treatment of N-allylic,N'-aryl ureas with a catalytic 1:1 mixture of di-tert-butyl-o-biphenylphoshphine gold(I) chloride and silver hexafluorophosphate (1 mol %) in chloroform at room temperature led to 5-exo hydroamination to form the corresponding imidazolidin-2-ones in excellent yield. In the case of N-allylic ureas that possessed an allylic alkyl, benzyloxymethyl, or acetoxymethyl substituent, gold(I)-catalyzed 5-exo hydroamination leads to formation of the corresponding trans-3,4-disubstituted imidazolidin-2-ones in excellent yield with ≥50:1 diastereoselectivity.
authors.affiliation: Duke University, French Family Science Center, Durham, North Carolina, USA. ; Tel: +1-919-660-1533.
authors.forename: Hao
authors.initials: H
authors.lastname: Li
authors.forename: Feijie
authors.initials: F
authors.lastname: Song
authors.forename: Ross A
authors.initials: RA
authors.lastname: Widenhoefer