Dual Catalytic Switchable Divergent Synthesis: An Asymmetric Visible-Light Photocatalytic Approach to Fluorine-Containing γ‑Keto Acid Frameworks

Herein, we describe
a novel and efficient method for constructing
a series of fluorine-containing γ-keto acid derivatives through
combining visible-light photoredox catalysis and chiral Lewis acid
catalysis. With this dual catalytic strategy, a variety of chiral
γ-keto amides containing a gem-difluoroalkyl
group and a series of fluorine-containing α,β-unsaturated-γ-keto
esters were successfully constructed with high stereoselectivities,
respectively. A series of experiments showed that the chemoselectivity
of this process was highly dependent on the fluorine reagents besides
the Lewis acid catalysts. This approach facilitates rapid access to
γ-keto acid derivatives, an important class of precursors for
pharmaceuticals, plasticizers, and various other additives.