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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 (CC BY 3.0).
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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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