Rhodium-Catalyzed Atroposelective C–H/C–H Cross-Coupling Reaction between 1-Aryl Isoquinoline Derivatives and Indolizines
Wenwen Zhang, Chen‐Xu Liu, Pusu Yang, Suzhen Zhang, Qing Gu, Shu‐Li You
Abstract
A rhodium-catalyzed asymmetric oxidative C-H/C-H cross-coupling reaction between 1-aryl isoquinolines and indolizines is disclosed. With a matched pair of SCpRh complex and chiral carboxylic acid, enantioselective two-fold C-H/C-H cross-coupling reactions between 1-aryl isoquinolines and indolizines provide a variety of axially chiral bi(hetero)aryls in excellent yields and enantioselectivity (up to 96% yield and 98% ee). Mechanistic studies suggest that both C-H cleavages are likely reversible.
Topics & Concepts
ChemistryRhodiumIsoquinolineEnantioselective synthesisArylCatalysisYield (engineering)Medicinal chemistryCoupling reactionStereochemistryCombinatorial chemistryOrganic chemistryMaterials scienceMetallurgyAlkylAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsAlkaloids: synthesis and pharmacology