Enantioselective Copper-Catalyzed Reductive Coupling of Alkenylazaarenes with Ketones

Catalytic enantioselective methods for the preparation
of chiral
azaarene-containing compounds are of high value. By combining the
utility of copper hydride catalysis with the ability of CN-containing
azaarenes to activate adjacent alkenes toward nucleophilic additions,
the enantioselective reductive coupling of alkenylazaarenes with ketones
has been developed. The process is tolerant of a wide variety of azaarenes
and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing
side chains with high levels of diastereo- and enantioselection.