Enantioselective Synthesis of Azoniahelicenes by Rh-Catalyzed C–H Annulation with Alkynes
Qiang Wang, Wenwen Zhang, Chao Zheng, Qing Gu, Shu‐Li You
Abstract
A rhodium(III)-catalyzed enantioselective C-H activation/annulation process is disclosed. With a catalyst derived from a chiral CpRh(III) complex and a chiral acid, the direct annulation reactions between 1-aryl isoquinoline derivatives and alkynes take place smoothly to afford a series of chiral azoniahelicenes in excellent yields and enantioselectivity (up to 99% yield and 96% ee). Mechanistic studies suggest that C-H bond cleavage may be the turnover-limiting step.
Topics & Concepts
ChemistryAnnulationEnantioselective synthesisIsoquinolineRhodiumCatalysisArylYield (engineering)Bond cleavageMedicinal chemistryStereochemistryOrganic chemistryCombinatorial chemistryMetallurgyMaterials scienceAlkylCatalytic C–H Functionalization MethodsSynthesis and Properties of Aromatic CompoundsAxial and Atropisomeric Chirality Synthesis