Enantioselective Friedel–Crafts alkylation of indole derivatives catalyzed by new Yb(OTf)3-pyridylalkylamine complexes as chiral Lewis acids

Guillaume Grach; Aurelia Dinut; Sylvain Marque; Jérôme Marrot; Richard Gil; Damien Prim

doi:10.1039/C0OB00461H

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Enantioselective Friedel–Crafts alkylation of indole derivatives catalyzed by new Yb(OTf)₃-pyridylalkylamine complexes as chiral Lewis acids†

Guillaume Grach,^ab Aurelia Dinut,^b Sylvain Marque,^a Jérôme Marrot,^a Richard Gil*^b and Damien Prim*^a

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* Corresponding authors

^a Université de Versailles-Saint-Quentin, Institut Lavoisier de Versailles UMR CNRS 8180, 45, avenue des États-Unis, France

^b Équipe de Catalyse Moléculaire, ICMMO, UMR CNRS 8182, Université Paris-Sud 11, France

Abstract

New Yb(OTf)₃-pyridylalkylamine complexes have been employed as chiral Lewis acids in the enantioselective Friedel–Crafts alkylation of indole derivatives with trifluoropyruvates. The influence of the substituents as well as the configuration of the ligands have been studied and allowed us to reach enantiomeric excesses up to 83%.

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Article information

DOI: https://doi.org/10.1039/C0OB00461H
Article type: Paper
Submitted: 20 Jul 2010
Accepted: 23 Sep 2010
First published: 11 Nov 2010

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Org. Biomol. Chem., 2011,9, 497-503

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Enantioselective Friedel–Crafts alkylation of indole derivatives catalyzed by new Yb(OTf)₃-pyridylalkylamine complexes as chiral Lewis acids

G. Grach, A. Dinut, S. Marque, J. Marrot, R. Gil and D. Prim, Org. Biomol. Chem., 2011, 9, 497 DOI: 10.1039/C0OB00461H

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Organic & Biomolecular Chemistry