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Issue 3, 2011
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Organocatalytic enantioselective desymmetrization of cyclic enonesviaphosphine promoted [3+2] annulations

Nathalie Pinto,a  Pascal Retailleau,a  Arnaud Voiturieza  and  Angela Marinetti*a 
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* Corresponding authors

a Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Centre de Recherche de Gif. 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France
E-mail: angela.marinetti@icsn.cnrs-gif.fr
Fax: +33 (0)1 69 07 72 47
Tel: +33 (0)1 69 82 30 36

Abstract

Phosphine catalyzed enantioselective [3+2] cyclizations on 4-substituted 2,6-diarylidenecyclohexanones and 2,4-diarylidene-bicyclo[3.1.0]hexan-3-ones take place with high diastereo- and enantioselectivity levels. The process affords spirocyclic compounds with excellent stereochemical control of up to five stereogenic centres.

Graphical abstract: Organocatalytic enantioselective desymmetrization of cyclic enonesviaphosphine promoted [3+2] annulations

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Publication details

The article was received on 10 Aug 2010, accepted on 12 Oct 2010 and first published on 09 Nov 2010


Article type: Communication
DOI: 10.1039/C0CC03164J
Citation: Chem. Commun., 2011,47, 1015-1017
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    Organocatalytic enantioselective desymmetrization of cyclic enonesviaphosphine promoted [3+2] annulations

    N. Pinto, P. Retailleau, A. Voituriez and A. Marinetti, Chem. Commun., 2011, 47, 1015
    DOI: 10.1039/C0CC03164J

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