Probing Chiral Sulfoximine Auxiliaries in Ru(II)-Catalyzed One-Pot Asymmetric C–H Hydroarylation and Annulations with Alkynes
Somratan Sau, Kallol Mukherjee, Koneti Kondalarao, Vincent Gandon, Akhila K. Sahoo
Abstract
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 (∼99% enantiomeric excess) and reused.
Topics & Concepts
Enantiopure drugChemistryStereocenterAnnulationIndolineIntramolecular forceEnantiomerSulfoxideEnantioselective synthesisCatalysisSurface modificationCombinatorial chemistryStereochemistryOrganic chemistryPhysical chemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques