Electrophile-Mediated Enantiospecific Cross-Couplings for the Synthesis of Heterocycles

Nitrogen-containing heterocycles are important motifs in a range of bioactive drug candidates and natural products. Hence sp2-sp3 cross coupling reactions of alkyl units to nitrogen-containing heterocycles are a desirable goal in synthesis. However, current approaches are typically limited in scope or display poor selectivity. The Aggarwal group has worked on cross couplings proceeding via boronate complexes, formed by reaction of boronic ester precursors with aryllithium reagents followed by activation of the aromatic ring (or heterocycle). This work seeks to develop this chemistry further for regioselective and enantiospecific sp2-sp3 cross-couplings to pyridines and other aromatic nitrogen-containing heterocycles.