Organocatalytic Asymmetric Friedel−Crafts Alkylation of Indoles with Simple α,β-Unsaturated Ketones

Giuseppe Bartoli, Marcella Bosco, Armando Carlone, Fabio Pesciaioli, Letizia Sambri, Paolo Melchiorre

Organic Letters · 2007 · 306 citations · 6 references

Concepts

Abstract

[structure: see text]. The first general and highly enantioselective organocatalytic Friedel-Crafts alkylation of indoles with simple alpha,beta-unsaturated ketones has been accomplished. Central to these studies has been the identification of a new catalyst amine salt, in which both the cation and the anion are chiral, that exhibits high reactivity and selectivity for iminium ion catalysis.

References

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