Asymmetric Transfer Hydrogenation of Unhindered and Non-Electron-Rich 1-Aryl Dihydroisoquinolines with High Enantioselectivity
Jonathan Barrios-Rivera, Yingjian Xu, Martin Wills
Abstract
The use of arene/Ru/TsDPEN catalysts bearing a heterocyclic group on the TsDPEN in the asymmetric transfer hydrogenation (ATH) of dihydroisoquinolines (DHIQs) containing meta- or para-substituted aromatic groups at the 1-position results in the formation of products of high enantiomeric excess. Previously, only 1-(ortho-substituted)aryl DHIQs, or with an electron-rich fused ring gave products with high enantioselectivity; therefore, this approach solves a long-standing challenge for imine ATH.
Topics & Concepts
ChemistryImineArylCatalysisEnantiomerRing (chemistry)Transfer hydrogenationEnantiomeric excessCombinatorial chemistryMedicinal chemistryEnantioselective synthesisOrganic chemistryStereochemistryRutheniumAlkylAsymmetric Hydrogenation and CatalysisSurface Chemistry and CatalysisCatalysis for Biomass Conversion