Rhodium‐Catalyzed Asymmetric Conjugate Addition of Organoboronic Acids to Carbonyl‐Activated Alkenyl Azaarenes
Huilong Zhu, Long Yin, Zhiqian Chang, Yuhan Wang, Xiaowei Dou
Abstract
Abstract The enantioselective synthesis of chiral azaarenes by rhodium‐catalyzed asymmetric conjugate addition of organoboronic acids to carbonyl‐activated alkenyl azaarenes was reported. Diverse chiral azaarenes were produced in up to 99% yield and with up to 99% ee (>60 examples). Catalytic asymmetric syntheses of dexchlorpheniramine and dexbrompheniramine were realized by using the developed method. magnified image
Topics & Concepts
ConjugateChemistryEnantioselective synthesisRhodiumCatalysisYield (engineering)Organic chemistryCombinatorial chemistryMetallurgyMathematicsMathematical analysisMaterials scienceCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCyclopropane Reaction Mechanisms