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

Abstract

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.