Binary Acid System for Asymmetric Regioselective 1,2- and
1,4- Addition

J. Lv; L. Zhang; Y. Zhou; Z. Nie; J.-P. Cheng; S. Luo

doi:10.1055/s-0030-1261057

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Synfacts 2011(10): 1101-1101
DOI: 10.1055/s-0030-1261057

Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions

Binary Acid System for Asymmetric Regioselective 1,2- and 1,4- Addition

Contributor(s): Hisashi Yamamoto, Patrick Brady
J. Lv, L. Zhang, Y. Zhou, Z. Nie, J.-P. Cheng, S. Luo*
Beijing National Laboratory for Molecular Sciences, P. R. of China

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Publication History

Publication Date:
20 September 2011 (online)

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Significance

The authors describe a highly enantioselective Friedel-Crafts alkylation of indoles with β,γ-unsaturated α-keto esters catalyzed by a combination of a chiral phosphoric acid and an indium(III) Lewis acid. Remarkably, InBr₃ catalyzes the 1,4-addition, while InF₃ catalyzes the 1,2-addition.