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Synthesis and resolution of 2-(diphenylphosphino)heptahelicene |
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| Authors: | Riadh El Abed,Jean-Pierre Genê t,Angela Marinetti |
| Affiliation: | 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, CNRS UMR 7573, E.N.S.C.P. 11, rue Pierre et Marie Curie, 75231 Paris Cedex 06, France c Institut de Chimie des Substances Naturelles, CNRS UPR 2301, 1, av. de la Terrasse, 91198 Gif-sur-Yvette Cedex, France |
| Abstract: | Palladium catalysed Heck couplings have been applied to the two-step synthesis of a stilbene derivative bearing a diphenylphosphine oxide function which represents a suitable precursor for the photochemical generation of the corresponding [7]-helicene. After reduction of the phosphine oxide, resolution of the monodentate helical phosphine has been performed by means of the ortho-metallated (R)-1-(naphthyl)ethylamine-palladium complex. A ruthenium complex of (heptahelicen-2-yl)diphenylphosphine has also been prepared and fully characterized. |
| Keywords: | Helicenes Phosphines Enantiomeric resolution Heck reaction Photocyclization |
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