As saturated heterocyclic building blocks become increasingly
popular
in medicinal chemistry and drug discovery programs, expansion of the
synthetic toolkit to novel stereofunctionalized heterocycles is a
priority. Herein, we report the development of a palladium-catalyzed
decarboxylative asymmetric allylic alkylation reaction to access a
broad range of enantioenriched α-difunctionalized 5- and 6-membered
sulfones from easily accessible racemic starting materials. The allylic
alkylation step was found to occur with high levels of enantioselectivity
as a result of a palladium-mediated dynamic kinetic resolution of
E
/
Z
enolate intermediates. This methodology
paves the way to hitherto unexplored stereodefined cyclic sulfones
for medicinal chemistry applications.
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