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

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

Publication , Journal Article

Li, H; Song, F; Widenhoefer, RA

Published in: Advanced synthesis & catalysis

April 2011

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.

Duke Scholars

Author Ross A. Widenhoefer Chemistry

Published In

Advanced synthesis & catalysis

DOI

10.1002/adsc.201000844

EISSN

1615-4169

ISSN

1615-4150

Publication Date

April 2011

Volume

353

Issue

Start / End Page

955 / 962

Related Subject Headings

Organic Chemistry
3405 Organic chemistry
0904 Chemical Engineering
0305 Organic Chemistry
0302 Inorganic Chemistry

Citation

APA

Chicago

ICMJE

MLA

NLM

Li, H., Song, F., & Widenhoefer, R. A. (2011). Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones. Advanced Synthesis & Catalysis, 353(6), 955–962. https://doi.org/10.1002/adsc.201000844

Li, Hao, Feijie Song, and Ross A. Widenhoefer. “Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones.” Advanced Synthesis & Catalysis 353, no. 6 (April 2011): 955–62. https://doi.org/10.1002/adsc.201000844.

Li H, Song F, Widenhoefer RA. Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones. Advanced synthesis & catalysis. 2011 Apr;353(6):955–62.

Li, Hao, et al. “Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones.” Advanced Synthesis & Catalysis, vol. 353, no. 6, Apr. 2011, pp. 955–62. Epmc, doi:10.1002/adsc.201000844.

Li H, Song F, Widenhoefer RA. Gold(I)-Catalyzed Intramolecular Hydroamination of N-Allylic,N'-Aryl Ureas to form Imidazolidin-2-ones. Advanced synthesis & catalysis. 2011 Apr;353(6):955–962.