Confronting the Challenge of Asymmetric Carbonyl Addition to Sterically Bulky Isatins: Upgrading Dirhodium(II)/Biphosphine Catalytic System
Wenjing Guo, Shuming Zhan, Han Yang, Zhenhua Gu
Abstract
Catalytic asymmetric addition of arylboronic acids to ketones is a powerful transformation for directly delivering chiral tertiary alcohols. However, there is no successful example of enantioselective addition to steric bulky isatins, which contain bulky substituent at the 4-position. To confront this challenge, in this work a dirhodium/(BTFM-Garphos) system was developed that showed extremely high activity and stereoselectivity, and the reactions were usually finished within a few minutes.
Topics & Concepts
ChemistrySteric effectsSubstituentStereoselectivityCatalysisEnantioselective synthesisRhodiumCombinatorial chemistryStereochemistryOrganic chemistryCyclopropane Reaction MechanismsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization Methods