Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.
Publication
, Journal Article
Li, H; Widenhoefer, RA
Published in: Organic letters
June 2009
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.
Duke Scholars
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
June 2009
Volume
11
Issue
12
Start / End Page
2671 / 2674
Related Subject Headings
- Urea
- Stereoisomerism
- Organic Chemistry
- Molecular Structure
- Imidazolidines
- Gold
- Cyclization
- Catalysis
- Bridged Bicyclo Compounds, Heterocyclic
- Amination
Citation
APA
Chicago
ICMJE
MLA
NLM
Li, H., & Widenhoefer, R. A. (2009). Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones. Organic Letters, 11(12), 2671–2674. https://doi.org/10.1021/ol900730w
Li, Hao, and Ross A. Widenhoefer. “Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.” Organic Letters 11, no. 12 (June 2009): 2671–74. https://doi.org/10.1021/ol900730w.
Li H, Widenhoefer RA. Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones. Organic letters. 2009 Jun;11(12):2671–4.
Li, Hao, and Ross A. Widenhoefer. “Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones.” Organic Letters, vol. 11, no. 12, June 2009, pp. 2671–74. Epmc, doi:10.1021/ol900730w.
Li H, Widenhoefer RA. Gold(I)-catalyzed intramolecular dihydroamination of allenes with N,N'-disubstituted ureas to form bicyclic imidazolidin-2-ones. Organic letters. 2009 Jun;11(12):2671–2674.
Published In
Organic letters
DOI
EISSN
1523-7052
ISSN
1523-7060
Publication Date
June 2009
Volume
11
Issue
12
Start / End Page
2671 / 2674
Related Subject Headings
- Urea
- Stereoisomerism
- Organic Chemistry
- Molecular Structure
- Imidazolidines
- Gold
- Cyclization
- Catalysis
- Bridged Bicyclo Compounds, Heterocyclic
- Amination