Combined Dynamic Kinetic Resolution and C-H Functionalization for Facile Synthesis of Non-Biaryl-Atropisomer-type Axially Chiral Organosilanes.

Despite asymmetric C-H functionalization has been available for the synthesis structurally diverse molecules, catalytic dynamic kinetic resolution (DKR) approaches to change racemic stereogenic axes remain synthetically challenges in this field. Here we present a concise palladium-catalyzed dynamic kinetic resolution combined with C-H functionalization involving olefination and alkynylation for the highly efficient synthesis of non-biaryl-atropisomer-type (NBA) axially chiral oragnosilanes. The chemistry proceeds through two different and distinct dynamic kinetic resolutions: first, an atroposelective C-H olefination or alkynylation produced axially chiral vinylsilanes or alkynylsilanes as a new family of non-biaryl atropisomers (NBA), and second, the extension of this DKR strategy to twofold o,o'-C-H functionalization led to the multifunctional axially chiral organosilicon compounds with up to >99% ee.