Multicomponent Synthesis of Chiral Bidentate Unsymmetrical Unsaturated N-Heterocyclic Carbenes: Copper-Catalyzed Asymmetric C Bond Formation

Claire Jahier-Diallo (1) , Marie S T Morin (1) , Pierre Queval (1) , Mathieu Rouen (1) , Isabelle Artur (1) , Pierre Querard (1) , Loic Toupet (2) , Christophe Crévisy (1) , Olivier Baslé (1) , Marc Mauduit (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 IPR - Institut de Physique de Rennes

A multicomponent strategy was applied to the synthesis of chiral bidentate unsaturated hydroxyalkyl- and carboxyalkyl-N-heterocyclic carbene (NHC) precursors. The newly developed low-cost chiral ligands derived from amino alcohols and amino acids were evaluated in copper-catalyzed asymmetric conjugated addition and asymmetric allylic alkylation, which afforded the desired tertiary and quaternary carbon stereocenters with excellent regio- and enantioselectivities (up to 99:1 e.r.).

Keywords: multicomponent synthesis; bifunctional ligands; chiral NHCs; asymmetric catalysis; quaternary carbon atoms

Domains: Chemical Sciences

Claire Jahier-Diallo, Marie S T Morin, Pierre Queval, Mathieu Rouen, Isabelle Artur, et al.. Multicomponent Synthesis of Chiral Bidentate Unsymmetrical Unsaturated N-Heterocyclic Carbenes: Copper-Catalyzed Asymmetric C Bond Formation. Chemistry - A European Journal, 2015, 21 (3), pp.993-7. ⟨10.1002/chem.201405765⟩. ⟨hal-01114852⟩