Dearomatization of Heteroarenium Salts with ArBpin Reagents. Application to the Total Synthesis of a Nuphar Alkaloid
Donovan J. Robinson, Kacey G. Ortiz, Nathan P. O’Hare, Rashad R. Karimov
Abstract
Rhodium-catalyzed enantioselective addition of aryl and heteroaryl boron pinacol esters to pyridinium and quinolinium salts is developed for the synthesis of enantioenrichred dihydroheteroarenes. The methodology has enabled the synthesis of 2-heteroaryl-substituted dihydropyridines in high yield and ee, which provided efficient synthetic access to a nuphar alkaloid.
Topics & Concepts
ChemistryAlkaloidPinacolEnantioselective synthesisPyridiniumReagentYield (engineering)RhodiumArylOrganic chemistryCombinatorial chemistryStereochemistryCatalysisAlkylMetallurgyMaterials scienceCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Synthesis and Catalysis