Diarylborinic Acid-Catalyzed Regioselective Ring Openings of Epoxy Alcohols with Pyrazoles, Imidazoles, Triazoles, and Other Nitrogen Heterocycles
Shrey P. Desai, Mark S. Taylor
Abstract
A method for regioselective ring openings of 3,4- and 2,3-epoxy alcohols with ambident nitrogen heterocycles is described. Using a diarylborinic acid catalyst, a single regioisomer is favored in couplings of nucleophile and electrophile partners that display low regioselectivity under conventional conditions. The method provides access to aromatic heterocycles bearing stereochemically defined, functionalized alkyl substituents, a product class similar in structure to medicinally relevant compounds such as the acyclic nucleoside analogues.
Topics & Concepts
RegioselectivityChemistryElectrophileRing (chemistry)NucleophileCatalysisStructural isomerAlkylOrganic chemistryCombinatorial chemistryCyclopropane Reaction MechanismsClick Chemistry and ApplicationsCatalytic C–H Functionalization Methods