Organic chemistry

Combinatorial chemistry

Optically active

Surface modification

Enantioselective synthesis

Catalysis

Physical chemistry

Chemistry

Indoline

Ruthenium

Journal of the American Chemical Society

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

Ruthenium-Catalyzed Enantioselective C–H Functionalization: A Practical Access to Optically Active Indoline Derivatives