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Enantiopure encaged Verkade's superbases: Synthesis,chiroptical properties,and use as chiral derivatizing agent |
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| Authors: | Jian Yang Bastien Chatelet Damien Hérault Véronique Dufaud Vincent Robert Stéphane Grass Jérôme Lacour Nicolas Vanthuyne Marion Jean Muriel Albalat Jean-Pierre Dutasta Alexandre Martinez |
| Affiliation: | 1. Aix Marseille Univ, CNRS, Centrale Marseille, iSm2, Marseille, France;2. Laboratoire de Chimie, Catalyse, Polymères, Procédés CNRS, UMR 5265, Université Claude Bernard Lyon1, Villeurbanne cedex, France;3. Laboratoire de Chimie Quantique Institut de Chimie, UMR CNRS 7177, Université de Strasbourg, Strasbourg, France;4. Department of Organic Chemistry, Quai Ernest Ansermet 30, University of Geneva, Geneva, Switzerland;5. Laboratoire de Chimie École Normale Supérieure de Lyon, CNRS, UCBL, 46 Allée d'Italie, Lyon, F-69364 France |
| Abstract: | Verkade's superbases, entrapped in the cavity of enantiopure hemicryptophane cages, have been synthesized with enantiomeric excess (ee) superior to 98%. Their absolute configuration has been determined by using electronic circular dichroism (ECD) spectroscopy. These enantiopure encaged superbases turned out to be efficient chiral derivatizing agents for chiral azides, underlining that the chirality of the cycloveratrylene (CTV) macrocycle induces different magnetic and chemical environments around the phosphazide functions. |
| Keywords: | chiral derivatizing agent ECD enantiopure cages Verkade's superbase |