Chiral-Directing-Group-Assisted Rhodium(III)-Catalyzed Asymmetric Addition of Inert Arene C-H Bond to Aldimines with Subsequent Intramolecular Cyclization

By using a chiral directing group, an asymmetric rhodium(III)-catalyzed C-H bond addition to aldimines followed by intramolecular cyclization to form chiral isoindolinones has been achieved (up to 68 % yield, up to 93 % ee). A three-component variant that resembles Mannich reaction was also realized (41 % yield, 83 % ee). Product elaborations and preliminary mechanistic studies were described.

Automated summary

By utilizing a chiral directing group, asymmetric rhodium(III)-catalyzed C-H bond addition to aldimines followed by intramolecular cyclization to form chiral isoindolinones has been achieved, with up to 68% yield and up to 93% ee. A three-component variant resembling Mannich reaction was also successful, with a yield of 41% and 83% ee. The study also includes product elaborations and preliminary mechanistic studies.