Synthesis of Optically Active Indoline Derivatives via Ruthenium(II)-Catalyzed Enantioselective C-H Functionalization

X. Cui, Z.Y. Li, C.L. Hetti Handi
Mississippi State University,
United States

Keywords: Ru(II)-catalysis, enantioselective C-H activation, hydroarylation, indoline

Summary:

Ru(II)-catalyzed enantioselective C-H activation/hydroarylation has been developed for the first time. It has demonstrated a highly enantioselective synthesis of indoline derivatives via catalytic C­H activation. Commercially available Ru(II) arene complexes and chiral a-methylamines were employed as highly enantioselective catalysts. Based on a sterically rigidified chiral transient directing group, multi-substituted indolines were produced in up to 92% yield with 96% ee. Further transformation of the resulting 4-formylindoline enabled an access to an optically active tricyclic compound that is of potential biological and pharmaceutical interest.