title: Double-Stereodifferentiation in Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair.
abstract: The first enantioselective metal-catalyzed [2 + 2 + 2] cycloaddition involving a double asymmetric induction has been devised. It relies on the use of an in situ generated chiral cationic rhodium(I) catalyst with a matched chiral ligand/chiral counterion pair. Careful optimization of the catalytic system, as well as of the reaction conditions, led to atroposelective [2 + 2 + 2] pyridone cycloadducts with high ee's up to 96%. This strategy outperformed those previously described involving a chiral ligand only or a chiral counterion only.
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Case 229, 4 Place Jussieu, Paris 75252 Cedex 05, France.
authors.forename: Mylène
authors.initials: M
authors.lastname: Augé
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Case 229, 4 Place Jussieu, Paris 75252 Cedex 05, France.
authors.forename: Alexandra
authors.initials: A
authors.lastname: Feraldi-Xypolia
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Case 229, 4 Place Jussieu, Paris 75252 Cedex 05, France.
authors.forename: Marion
authors.initials: M
authors.lastname: Barbazanges
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Case 229, 4 Place Jussieu, Paris 75252 Cedex 05, France.
authors.forename: Corinne
authors.initials: C
authors.lastname: Aubert
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Case 229, 4 Place Jussieu, Paris 75252 Cedex 05, France.
authors.forename: Louis
authors.initials: L
authors.lastname: Fensterbank
authors.affiliation: ‡ICMMO, UMR CNRS 8182, Univ Paris-Sud 11, 91405 Orsay, France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Gandon
authors.affiliation: ‡ICMMO, UMR CNRS 8182, Univ Paris-Sud 11, 91405 Orsay, France.
authors.forename: Emilie
authors.initials: E
authors.lastname: Kolodziej
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire, UMR CNRS 8232, Case 229, 4 Place Jussieu, Paris 75252 Cedex 05, France.
authors.forename: Cyril
authors.initials: C
authors.lastname: Ollivier