Copper-Catalyzed Regio- and Diastereoselective Additions of Boron-Stabilized Carbanions to Heteroarenium Salts: Synthesis of Azaheterocycles Containing Contiguous Stereocenters
Rajender Nallagonda, Rashad R. Karimov
Abstract
Nucleophilic addition of diborylalkyl reagents to N-alkyl or N-acylpyridinium and related heteroarenium salts has been developed as a key step for the synthesis of nonaromatic nitrogen heterocycles that contain contiguous stereogenic centers. Derivatization of the dihydropyridine products for the synthesis of tetrahydropyridines and piperidines have also been described.
Topics & Concepts
StereocenterChemistryReagentCarbanionNucleophileCatalysisAlkylDerivatizationOrganic chemistryCombinatorial chemistryEnantioselective synthesisHigh-performance liquid chromatographyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry