Catalytic asymmetric deuterosilylation of exocyclic olefins with mannose-derived thiols and deuterium oxide

Abstract

Here we report a photochemical approach for asymmetric deuterosilylation of exocyclic olefins by utilizing mannose-derived thiols as the chiral catalyst and inexpensive deuterium oxide as the deuterium source. DFT computational studies reveal that multiple non-covalent interactions between the thiol catalyst and the radical adduct are responsible for controlling the enantioselectivity of the reaction.