Skip to main content
Journal cover image

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, 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.
Journal cover image

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