Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.
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.
Li
Hao
H
Duke University, Department of Chemistry, French Family Science Center, Durham, North Carolina 27708-0346, USA.
Widenhoefer
Ross A
RA
D000466:Alkadienes / Q000737:chemistry*; D000586:Amination; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D048289:Imidazolidines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014508:Urea / Q000737:chemistry*
D000466:Alkadienes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D048289:Imidazolidines; C025947:propadiene; D006046:Gold; D014508:Urea