design of new chiral phosphorus ligands and catalysts for the

DESIGN OF NEW CHIRAL PHOSPHORUS LIGANDS AND
CATALYSTS FOR THE DEVELOPMENT OF INNOVATIVE
STEREOSELECTIVE METHODOLOGIES
Arnaud VOITURIEZ
Institut de Chimie des Substances Naturelles, CNRS, Centre de Recherche de Gif.
1, av. de la terrasse, 91198 Gif-sur-Yvette, France.
[email protected]
The design of new chiral phosphorus ligands and catalysts is often the key for the
efficient development of innovative catalytic processes. This encourages us to investigate
synthetic approaches to new families of enantiomerically pure chiral phosphines whose
properties are then evaluated in targeted challenging catalytic reactions. We present here the
synthesis and the use of chiral trivalent phosphine with planar chirality, called FerroPHANE,
which has been successfully applied as nucleophilic catalyst in enantioselective [3 + 2]
cyclisation reactions.1 The synthesis of phosphorus-containing helicenes2 will be also
presented.
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1. (a) Pinto, N.; Neel, M.; Panossian, A.; Retailleau, P.; Frison, G.; Voituriez, A.; Marinetti, A. Chem. Eur. J.
2010, 16, 1033. (b) Voituriez, A.; Pinto, N.; Neel, M.; Retailleau, P.; Marinetti A. Chem. Eur. J. 2010, 16,
12541. (c) Pinto, N.; Retailleau, P.; Voituriez, A.; Marinetti A. Chem. Commun. 2011, 45, 1015. (d) Duvvuru,
D.; Pinto, N.; Gomez, C.; Betzer, J.-F.; Retailleau, P.; Voituriez, A.; Marinetti, A. Adv. Synth. Catal. 2012,
354, 408. (e) Gomez, C.; Gicquel, M.; Carry, J.-C.; Schio, L.; Retailleau, P.; Voituriez, A.; Marinetti, A. J.
Org. Chem. 2013, 78, 1488. (f) Gomez, C.; Betzer, J.-F.; Voituriez, A.; Marinetti, A. Chem. Cat. Chem.
2013, DOI: 10.1002/cctc.201200442.
2. (a) Yavari, K.; Moussa, S.; Ben Hassine, B.; Retailleau, P.; Voituriez, A.; Marinetti, A. Angew. Chem. Int.
Ed. 2012, 51, 6748. (b) Yavari, K.; Retailleau, P.; Voituriez, A.; Marinetti, A. Chem. Eur. J. 2013, accepted.