Enantioselective allylation, crotylation, and reverse prenylation of substituted isatins: iridium-catalyzed C-C bond-forming transfer hydrogenation.

Transfer hydrogenation of substituted isatins in the presence of allyl acetate, α-methyl allyl acetate or 1,1,-dimethylallene employing an -cyclometallated iridium catalyst modified by CTH-()-P-PHOS provides products of carbonyl allylation, crotylation and reverse prenylation, respectively, in highly enantiomerically enriched form. These studies represent the first use of activated ketones as electrophilic partners in asymmetric C-C bond forming transfer hydrogenation. [Image: see text]