title: Multicomponent synthesis of chiral bidentate unsymmetrical unsaturated N-heterocyclic carbenes: copper-catalyzed asymmetric C-C bond formation.
abstract: 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.).
authors.affiliation: Ecole Nationale Supérieure de Chimie de Rennes, UMR CNRS 6226, 11 Allée de Beaulieu, CS 50837, 35708, Rennes Cedex 7 (France).
authors.forename: Claire
authors.initials: C
authors.lastname: Jahier-Diallo
authors.forename: Marie S T
authors.initials: MS
authors.lastname: Morin
authors.forename: Pierre
authors.initials: P
authors.lastname: Queval
authors.forename: Mathieu
authors.initials: M
authors.lastname: Rouen
authors.forename: Isabelle
authors.initials: I
authors.lastname: Artur
authors.forename: Pierre
authors.initials: P
authors.lastname: Querard
authors.forename: Loic
authors.initials: L
authors.lastname: Toupet
authors.forename: Christophe
authors.initials: C
authors.lastname: Crévisy
authors.forename: Olivier
authors.initials: O
authors.lastname: Baslé
authors.forename: Marc
authors.initials: M
authors.lastname: Mauduit
keywords: asymmetric catalysis; bifunctional ligands; chiral NHCs; multicomponent synthesis; quaternary carbon atoms