Catalytic Asymmetric Ionic Hydrogenation of α-Alkyl Styrenes.

ABSTRACT: Over the past two decades, chemists have made significant advances in the field of catalytic asymmetric transfer hydrogenation of various unsaturated compounds with biomimetic hydrogen donors. The reduction of carbon-carbon double bonds, however, has been limited to activated substrate classes, such as enals, enones, nitroolefins, or α-(2-hydroxyaryl) styrenes. Here we report a highly enantioselective Brønsted acid-catalyzed ionic hydrogenation of α-alkyl styrenes using a hydrosilane in combination with a protic additive. Mechanistic and computational investigations support a pathway proceeding through a carbocation intermediate and a transient silylated catalyst species, with catalyst turnover dependent on the presence of a protic additive. Moreover, the exemplary stereoconvergent reducti

SUBMITTER: Leinung W 

PROVIDER: S-EPMC12412155 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature