Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2011:7:1070-4.
doi: 10.3762/bjoc.7.123. Epub 2011 Aug 8.

Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation

Jingjing Wu  1 , Hui Li, Song Cao
Affiliations

Novel synthesis of pseudopeptides bearing a difluoromethyl group by Ugi reaction and desulfanylation

Jingjing Wu et al. Beilstein J Org Chem. 2011.

Abstract

Thirteen difluoromethyl-containing pseudopeptides were synthesized by Ugi reaction using the novel building block 2,2-difluoro-2-(phenylthio)acetic acid (2) as one component, followed by removal of the phenylsulfanyl protecting group in the presence of tributyltin hydride and azobisisobutyronitrile.

Keywords: Ugi reaction; difluoromethyl functionality; gem-difluoromethylene-containing acid; pseudopeptides; reductive cleavage.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Two examples of bioactive pseudopeptides bearing a CF2H group.
Scheme 1
Scheme 1
Synthesis of difluoromethyl-containing pseudopeptides (4a–m) by Ugi reaction and desulfanylation.
Scheme 2
Scheme 2
The Ugi reaction of aniline, benzaldehyde, (isocyanomethyl)benzene with acetic acid, difluoroacetic acid and trifluoroacetic acid in methanol or under solvent-free conditions.
Scheme 3
Scheme 3
Synthesis of 2,2-difluoro-2-(phenylthio)acetic acid (2).
See this image and copyright information in PMC

References

    1. Qiu X, Meng W, Qing F. Tetrahedron. 2004;60:6711–6745. doi: 10.1016/j.tet.2004.05.051. - DOI
    1. Jäckel C, Koksch B. Eur J Org Chem. 2005:4483–4503. doi: 10.1002/ejoc.200500205. - DOI
    1. Meng H, Kumar K. J Am Chem Soc. 2007;129:15615–15622. doi: 10.1021/ja075373f. - DOI - PubMed
    1. Couve-Bonnaire S, Cahard D, Pannecoucke X. Org Biomol Chem. 2007;5:1151–1157. doi: 10.1039/b701559c. - DOI - PubMed
    1. Mlostoń G, Obijalska E, Heimgartner H. J Fluorine Chem. 2010;131:829–843. doi: 10.1016/j.jfluchem.2010.05.014. - DOI - PMC - PubMed

LinkOut - more resources