Ir-catalyzed asymmetric transfer hydrogenation of racemic quinolinyl-substituted tertiary alcohols

Abstract

We report herein a highly efficient stereodivergent reaction of racemic quinolinyl-substituted tertiary alcohols via Ir-catalyzed asymmetric transfer hydrogenation, which affords structurally unique chiral 1,2,3,4-tetrahydroquinolines bearing both endo- and exocyclic chirality. By modulation of the configuration of the catalyst, all four diastereomers can be accessed with excellent ee and dr (generally >95% ee). Through reoxidation, the products can be converted into enantiopure starting materials, thus realizing a formal resolution of challenging tertiary alcohols.