Synfacts 2009(4): 0404-0404  
DOI: 10.1055/s-0028-1087904
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Zirconium-Catalyzed Friedel-Crafts Alkylation of Pyrrole

Contributor(s): Mark Lautens, Jacki Kitching
G. Blay, I. Fernández, A. Monleón, J. R. Pedro*, C. Vila
Universitat de València, Spain
Further Information

Publication History

Publication Date:
23 March 2009 (online)

Significance

The zirconium-catalyzed enantio­selective Friedel-Crafts alkylation of pyrrole with 2,2,2-trifluoroacetophenones is reported. The resulting pyrroles with a trifluoromethyl-substituted tertiary alcohol moiety are afforded in high yield and enantioselectivity. In addition, the BINOL-type ligands are commercially available in both enantiomeric forms. Thus, this procedure enables ready access to both enantiomers of the target compounds.