Kinetic resolution of sulfur-stereogenic sulfoximines by Pd( <scp>ii</scp> )–MPAA catalyzed C–H arylation and olefination
Kallol Mukherjee, Nicolás Grimblat, Somratan Sau, Koushik Ghosh, Majji Shankar, Vincent Gandon, Akhila K. Sahoo
Abstract
-discriminating C(aryl)-H activation. This method provides access to a wide range of enantiomerically enriched unreacted aryl-pyridyl-sulfoximine precursors and C(aryl)-H alkenylation/arylation products in good yields with high enantioselectivity (up to >99% ee), and selectivity factor up to >200. The coordination preference of the directing group, ligand effect, geometry constraints, and the transient six-membered concerted-metalation-deprotonation species dictate the stereoselectivity; DFT studies validate this hypothesis.
Topics & Concepts
StereocenterCatalysisChemistrySulfurKinetic resolutionStereochemistryCombinatorial chemistryBiochemistryOrganic chemistryEnantioselective synthesisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques