Double-Stereodifferentiation in Rhodium-Catalyzed [2+2+2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2015

Double-Stereodifferentiation in Rhodium-Catalyzed [2+2+2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair

Résumé

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 ees up to 96%. This strategy outperformed those previously described involving a chiral ligand only or a chiral counterion only.

Domaines

Chimie organique
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Dates et versions

hal-01397964 , version 1 (16-11-2016)

Identifiants

Citer

Mylène Augé, Alexandra Feraldi-Xypolia, Marion Barbazanges, Corinne Aubert, Louis Fensterbank, et al.. Double-Stereodifferentiation in Rhodium-Catalyzed [2+2+2] Cycloaddition: Chiral Ligand/Chiral Counterion Matched Pair. Organic Letters, 2015, 17 (15), pp.3754-3757. ⟨10.1021/acs.orglett.5b01738⟩. ⟨hal-01397964⟩
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