Synthesis of a Configurationally Locked [5]Helicene Derivative

Riadh El Abed; Béchir Ben Hassine; Jean-Pierre Genêt; Mohamed Gorsane; Jonathan Madec; Louis Ricard; Angela Marinetti

doi:10.1055/s-2004-831229

PAPER

Synthesis of a Configurationally Locked [5]Helicene Derivative

Riadh El Abed^a, Béchir Ben Hassine*^a, Jean-Pierre Genêt*^b, Mohamed Gorsane^a, Jonathan Madec^b, Louis Ricard^c, Angela Marinetti*^b
^a Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène, Faculté des Sciences de Monastir, Avenue de l’Environnement, 5019 Monastir, Tunisia
^b Laboratoire de Synthèse Sélective Organique et Produits Naturels, UMR 7573, E.N.S.C.P. 11, rue Pierre et Marie Curie, 75231 Paris Cedex 06, France
Fax: +33(1)44071062; e-Mail: marinet@ext.jussieu.fr;
^c Laboratoire Hétéroéléments et Coordination, Ecole Polytechnique, 91128 Palaiseau Cedex, France

Abstract

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Abstract

The photochemical cyclisation-dehydrogenation of the bis-styrylbenzene 3, where the terminal aryl moieties are connected by a suitable chiral tether derived from 1,3-pentanediol, led to a chiral, configurationally locked [5]helicene derivative. An X-ray diffraction study showed that an (S,S)-configuration of the chiral auxiliary induces a (P)-configuration of the helical framework.

Key words

helical structures - chiral auxiliaries - diols - photochemistry - stereoselectivity

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