Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.
Journal Article
Reaction of N-delta-allenyl urea 1 with a catalytic 1:1 mixture of gold(I) N-heterocyclic carbene complex (5)AuCl [5 = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidine] and AgPF(6) at room temperature for 2 h led to isolation of bicyclic imidazolidin-2-one 4 in 93% yield with >or=98% diastereomeric purity. Gold-catalyzed dihydroamination was effective for a number of N-delta- and N-gamma-allenyl ureas to form the corresponding bicyclic imidazolidin-2-ones in good yield with high diastereoselectivity.
Full Text
Duke Authors
Cited Authors
- Li, H; Widenhoefer, RA
Published Date
- June 2009
Published In
Volume / Issue
- 11 / 12
Start / End Page
- 2671 - 2674
PubMed ID
- 19514795
Pubmed Central ID
- 19514795
Electronic International Standard Serial Number (EISSN)
- 1523-7052
International Standard Serial Number (ISSN)
- 1523-7060
Digital Object Identifier (DOI)
- 10.1021/ol900730w
Language
- eng