Probing Chiral Sulfoximine Auxiliaries in Ru(II)-Catalyzed One-Pot Asymmetric C-H Hydroarylation and Annulations with Alkynes

Developed herein is a chiral sulfoximine-enabled Ru-(II)-catalyzed asymmetric C-H activation/functionalization involving intramolecular hydroarylation and functionalization/annulation of alkynes. This process constructs dihydrobenzofuran- or indoline-fused isoquinolinones having a tertiary or quaternary stereocenter with good yields and enantioselectivities (up to 97:3 enantiomeric ratio). The chiral sulfoxide precursor used in synthesizing the enantiopure sulfoximines is spontaneously eliminated during the reaction. It can be recovered without losing enantiopurity (similar to 99% enantiomeric excess) and reused.

Automated summary

A chiral sulfoximine-enabled Ru-(II)-catalyzed asymmetric C-H activation/functionalization process has been developed for the synthesis of dihydrobenzofuran- or indoline-fused isoquinolinones with a tertiary or quaternary stereocenter. The method achieves high yields and enantioselectivities (up to 97:3 enantiomeric ratio) and allows for the recovery and reuse of the chiral sulfoxide precursor.