Asymmetric Friedel–Crafts/Michael Reaction of Indoles and Pyrroles with Coumarin-3-carbonylates

Victor G. Desyatkin; Irina P. Beletskaya

doi:10.1055/s-0036-1589024

Synthesis, Table of Contents

Synthesis 2017; 49(18): 4327-4334
DOI: 10.1055/s-0036-1589024

paper

Asymmetric Friedel–Crafts/Michael Reaction of Indoles and Pyrroles with Coumarin-3-carbonylates

Victor G. Desyatkin

Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, Moscow, 119991, Russian Federation Email: beletska@org.chem.msu.ru

,

Irina P. Beletskaya*

Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, Moscow, 119991, Russian Federation Email: beletska@org.chem.msu.ru

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Abstract

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Abstract

Asymmetric Friedel–Crafts reactions of indoles or pyrroles with coumarin-3-carboxylates catalyzed by Cu(OTf)₂ complexes with chiral bis(oxazoline) ligands have been developed. The highest ee (up to 82%) was achieved for indole with a nitro derivative of coumarin-3-carboxylate.

Key words

enantioselective catalysis - BOX ligands - copper - 3,4-dihydrocoumarins - asymmetric Friedel–Crafts reaction

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References

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