Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ll)–MPAA catalyzed C–H arylation and olefination - École polytechnique Accéder directement au contenu
Article Dans Une Revue Chemical Science Année : 2021

Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ll)–MPAA catalyzed C–H arylation and olefination

Résumé

A direct Pd(II)-catalyzed kinetic resolution of heteroaryl-enabled sulfoximines through an ortho-C–H alkenylation/arylation of arenes has been developed. The coordination of the sulfoximine pyridyl-motif and the chiral amino acid MPAA ligand to the Pd(II)-catalyst controls the enantio-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
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Dates et versions

hal-04477876 , version 1 (24-05-2024)

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Kallol Mukherjee, Nicolas Grimblat, Somratan Sau, Koushik Ghosh, Majji Shankar, et al.. Kinetic resolution of sulfur-stereogenic sulfoximines by Pd(ll)–MPAA catalyzed C–H arylation and olefination. Chemical Science, 2021, 12 (44), pp.14863-14870. ⟨10.1039/D1SC04299H⟩. ⟨hal-04477876⟩
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