Readily Accessible Unsymmetrical Unsaturated 2,6-Diisopropylphenyl N-Heterocyclic Carbene Ligands. Applications in Enantioselective Catalysis

Robert Tarrieu (1) , Adrien Dumas (1) , Jompol Thongpaen (1) , Thomas Vives (1) , Thierry Roisnel (1) , Vincent Dorcet (1) , Christophe Crevisy (1) , Olivier Baslé (1) , Marc Mauduit (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

A new multicomponent procedure was applied to the synthesis of (a)chiral bulky unsymmetrical unsaturated 2,6-diisopropylphenyl N-heterocyclic carbene (NHC) precursors with excellent selectivity (up to 95%) and good yields. This approach offers access to new chiral NHC ligands, which have found successful applications in both copper-catalyzed asymmetric allylic alkylation and copper-catalyzed asymmetric borylation.

Domaines: Chimie organique; Catalyse

Robert Tarrieu, Adrien Dumas, Jompol Thongpaen, Thomas Vives, Thierry Roisnel, et al.. Readily Accessible Unsymmetrical Unsaturated 2,6-Diisopropylphenyl N-Heterocyclic Carbene Ligands. Applications in Enantioselective Catalysis. Journal of Organic Chemistry, 2017, 82 (4), pp.1880-1887. ⟨10.1021/acs.joc.6b02888⟩. ⟨hal-01475697⟩