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. 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.

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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).
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