Catalyst-Controlled Enantioselective and Regiodivergent Addition of Aryl Boron Nucleophiles to N-Alkyl Nicotinate Salts
Kacey G. Ortiz, Jordan J. Dotson, Donovan J. Robinson, Matthew S. Sigman, Rashad R. Karimov
Abstract
Dihydropyridines are versatile building blocks for the synthesis of pyridines, tetrahydropyridines, and piperidines. Addition of nucleophiles to activated pyridinium salts allows synthesis of 1,2-, 1,4-, or 1,6-dihydropyridines; however, this process often leads to a mixture of constitutional isomers. Catalyst-controlled regioselective addition of nucleophiles to pyridiniums has the potential to solve this problem. Herein, we report that the regioselective addition of boron-based nucleophiles to pyridinium salts can be accomplished by the choice of a Rh catalyst.
Topics & Concepts
ChemistryNucleophilePyridiniumRegioselectivityEnantioselective synthesisCatalysisArylAlkylOrganic chemistryBoronCombinatorial chemistryMedicinal chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry