Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones.

Published

Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Li, H; Song, F; Widenhoefer, RA

Published Date

  • April 2011

Published In

Volume / Issue

  • 353 / 6

Start / End Page

  • 955 - 962

PubMed ID

  • 21709731

Pubmed Central ID

  • 21709731

Electronic International Standard Serial Number (EISSN)

  • 1615-4169

International Standard Serial Number (ISSN)

  • 1615-4150

Digital Object Identifier (DOI)

  • 10.1002/adsc.201000844

Language

  • eng