Synfacts 2007(9): 0948-0948  
DOI: 10.1055/s-2007-968862
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Friedel-Crafts Alkylation of Indole with Simple Enones

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
G. Blay, I. Fernandez, J. R. Pedro*, C. Vila
Universitat de València, Spain
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23. August 2007 (online)


This paper describes the highly enantioselective Friedel-Crafts alkylation of indoles and pyrrole with simple enones catalyzed by a Zr(IV)-BINOL complex. While the authors state that the reaction is limited to enones with aromatic or heteroaromatic R2 groups, nearly all substrates give consistenly high yields and ee values. Interestingly, the corresponding titanium and scandium complexes did not provide products in high enantioselectivities.