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Synfacts 2011(11): 1217-1217
DOI: 10.1055/s-0031-1289183
DOI: 10.1055/s-0031-1289183
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Zirconium-Catalyzed Enantioselective Friedel-Crafts Alkylation of Pyrroles
G. Blay, I. Fernández, M. C. Muñoz, J. R. Pedro*, A. Recuenco, C. Vila
Universitat de València and Universitat Politècnica de València, Spain
Further Information
Publication History
Publication Date:
19 October 2011 (online)
Significance
The enantioselective Friedel-Crafts reaction with pyrrole is challenging due to its racemization through azafulvenium intermediates. Previously, CF3-substituted carbonyl compounds were used to destabilize the intermediate and gave desirable products enantioselectively. In this paper, the authors succeeded in employing α-keto esters to suppress the racemization. This is the first example of the synthesis of a pyrrole-substituted tertiary alcohol which is not attached to a CF3 group.