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Molecules 2009, 14(8), 3030-3036; doi:10.3390/molecules14083030
Article

Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids

1
, 2
 and 1,*
1 Dipartimento di Chimica, Università di Salerno, Via Ponte Don Melillo 84084, Fisciano,Salerno, Italy 2 Istituto di Chimica Biomolecolare-CNR Trav. La Crucca3, Reg. Baldinca 07040Li Punti, Sassari, Italy
* Author to whom correspondence should be addressed.
Received: 22 July 2009 / Revised: 6 August 2009 / Accepted: 10 August 2009 / Published: 13 August 2009
(This article belongs to the Special Issue Asymmetric Synthesis)
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Abstract

The reaction of indole with chalcones, to give Michael-type adducts, was found to occur with good efficiency (up to 98% yield) and moderate enantioselectivity (up to 52% e.e.) in the presence of a chiral BINOL-based phosphoric acid. Furthermore, the alkylation products can be obtained in much higher e.e.s after one only crystallization.
Keywords: asymmetric Friedel-Crafts; indole; chiral phosphoric acids asymmetric Friedel-Crafts; indole; chiral phosphoric acids
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Scettri, A.; Villano, R.; Acocella, M.R. Asymmetric Friedel-Crafts Alkylation of Indole with Chalcones Catalyzed by Chiral Phosphoric Acids. Molecules 2009, 14, 3030-3036.

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