Asymmetric catalytic Friedel–Crafts alkylation with arenes and heteroarenes: construction of 3,3-disubstituted oxindoles

Abstract

Asymmetric synthesis of enantioenriched C3-arylated oxindoles bearing tetrasubstituted stereocenter has been achieved using chiral N,N′-dioxide/transition metal complex which promote Friedel–Crafts alkylation of 3-bromo-3-substituted oxindoles with arenes and heteroarenes i.e., anisole...

Reversal of enantioselectivity by tuning the ring size of ProPhenol

“…With a small ring, ( S , S )- L 4 -3 was more sensitive to the steric effect of the proximal 4-chloro group. On the basis of the above experimental results and previous studies on asymmetric Friedel–Crafts alkylation with arenes, 52 two plausible transition states (TS) were suggested to account for the enantiodivergence (Fig. 4C).…”

Cu(II)‐Catalyzed Enantioselective Aza‐Friedel‐Crafts Reaction of 1‐Naphthols and Electron‐Rich Phenols with Isatin‐Derived Ketimines

“…As a consequence, efforts have been made in enantioselective construction of different chiral 3-substituted-3-amino-2-oxyindoles. [5] Among the variety of methods developed, asymmetric catalytic aza-Friedel-Crafts reactions of (hetero)aromatic compounds with isatin-derived ketimines [6] or 3-bromo-3-substituted oxindoles [7] has emerged as one of the most efficient routes to such biologically important chiral 3-substituted-3amino-2-oxyindole derivatives. To date, considerable efforts have been focused on the reactions of indoles and pyrroles, and studies on the utilization of less active naphthols or electron-rich phenols are relatively less pursued.…”