Kinetic Resolution of Spiroindolines through Ir-Catalyzed Asymmetric Allylative Ring-Opening Reaction

Kinetic resolution of racemic spiroindolines with s factors of <= 15200 has been developed to access enantiomerically enriched indoleannulated medium-sized lactams and spiroindolines through Ir- catalyzed asymmetric allylative ring-opening reaction. Density functional theory calculations support the idea that the accurate discrimination of two spiroindoline enantiomers by (eta(3)-allyl)-iridium(III) species and the perfect central-to-axial chirality conversion during C-C bond fragmentation ensure the stereoselective formation of two contiguous stereogenic centers and one axis in the mediumsized lactams.

Automated summary

A kinetic resolution method has been developed for racemic spiroindolines with s factors <= 15200, allowing the access to enantiomerically enriched indoleannulated medium-sized lactams and spiroindolines through Ir-catalyzed asymmetric allylative ring-opening reaction. Density functional theory calculations support the accurate discrimination of two spiroindoline enantiomers by (eta(3)-allyl)-iridium(III) species and ensure the stereoselective formation of two contiguous stereogenic centers and one axis in the medium-sized lactams.