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Chiral atrop Copper-NHC (ChemRxiv).pdf (1.41 MB)

From Prochiral N-Heterocyclic Carbenes (NHC) to Optically Pure Copper Complexes: New Opportunities in Asymmetric Catalysis

submitted on 04.07.2019, 14:11 and posted on 05.07.2019, 15:57 by Lingyu Kong, Jennifer Morvan, Delphine Pichon, Marion Jean, Muriel Albalat, Thomas Vives, Sophie Colombel-Rouen, Michel Giorgi, Christophe Crévisy, Didier Nuel, Paola Nava, Stéphane Humbel, Nicolas Vanthuyne, Marc MAUDUIT, Hervé Clavier
Well-defined optically pure copper-complexes are obtained from prochiral N- Heterocyclic Carbene (NHC) ligands. As predicted by DFT calculations, our strategy capitalizes on the formation of a metal-carbene bond which induces axial chirality. Configurationally stable (Sa)- and (Ra)-atropisomers of various Cu-complexes are isolated by preparative chiral HPLC in nearly quantitative yields and excellent optical purities (>99.5%). Their catalytic performances are illustrated in asymmetric allylic alkylation with high regioselectivity and enantioinductions. Importantly, the carbene transfer from an optically pure Cu-complex to gold or palladium center reveals, for the first time, a full stereoretentivity, supporting the hypothesis of an associative mechanism for the transmetalation.


Email Address of Submitting Author


Univ Rennes, ENSCR, CNRS, ISCR UMR 6226



ORCID For Submitting Author


Declaration of Conflict of Interest

No Conflict of Interest