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Journal Articles Chirality Year : 2022

Transition metal complexes bearing atropisomeric saturated NHC ligands

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Abstract

From achiral imidazolinium salts, chiral transition metal complexes containing an N-heterocyclic carbene (NHC) ligand were prepared (metal = palladium, copper, silver, gold, rhodium). Axial chirality in these complexes results from the formation of the metal-carbene bond leading to the restriction of rotation of dissymmetric N-aryl substituents about the C–N bond. When these complexes exhibited a sufficient configurational stability, a resolution by chiral high-performance liquid chromatography (HPLC) on preparative scale enabled isolation of enantiomers with excellent enantiopurities (>99% ee) and good yields. A study of the enantiomerization barriers revealed the effect of the backbone nature as well as the type of transition metal on its values. Nevertheless, the evaluation of palladium-based complexes in asymmetric intramolecular α-arylation of amides demonstrated that the ability to induce an enantioselectivity cannot be correlated to the configurational stability of the precatalysts.
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Dates and versions

hal-03500191 , version 1 (21-12-2021)

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Mariia Savchuk, Lucas Bocquin, Muriel Albalat, Marion Jean, Nicolas Vanthuyne, et al.. Transition metal complexes bearing atropisomeric saturated NHC ligands. Chirality, 2022, 34 (1), pp.13-26. ⟨10.1002/chir.23378⟩. ⟨hal-03500191⟩

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