Chiral Phosphate in Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both? - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2016

Chiral Phosphate in Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both?

Résumé

Investigations based on NMR spectroscopy, mass spectrometry, and DFT calculations shed light on the metallic species generated in the rhodium-catalyzed asymmetric [2+2+2] cycloaddition reaction between diynes and isocyanates with the chiral phosphate TRIP. The catalytic mixture comprising [{Rh(cod)Cl}2 ], 1,4-diphenylphosphinobutane (dppb), and Ag(S)-TRIP actually gives rise to two species, both having an effect on the stereoselectivity. One is a rhodium(I) complex in which TRIP is a weakly coordinating counterion, whereas the other is a bimetallic Rh/Ag complex in which TRIP is a strongly coordinating X-type ligand.

Domaines

Chimie
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Dates et versions

hal-01314957 , version 1 (12-05-2016)

Identifiants

Citer

Marion Barbazanges, Elsa Caytan, Denis Lesage, Corinne Aubert, Louis Fensterbank, et al.. Chiral Phosphate in Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition: Ligand, Counterion, or Both?. Chemistry - A European Journal, 2016, 22 (25), pp.8553-8558. ⟨10.1002/chem.201601188⟩. ⟨hal-01314957⟩
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