Liang Hui, Xu Guo-Qiang, Feng Zhi-Tao, Wang Zhu-Yin, Xu Peng-Fei
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , P. R. China.
J Org Chem. 2019 Jan 4;84(1):60-72. doi: 10.1021/acs.joc.8b02316. Epub 2018 Dec 13.
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.
在此，我们描述了一种通过结合可见光光氧化还原催化和手性路易斯酸催化来构建一系列含氟γ-酮酸衍生物的新颖且高效的方法。采用这种双催化策略，分别成功构建了多种含有偕二氟烷基的手性γ-酮酰胺和一系列具有高立体选择性的含氟α,β-不饱和γ-酮酯。一系列实验表明，除了路易斯酸催化剂外，该过程的化学选择性高度依赖于氟试剂。这种方法有助于快速获得γ-酮酸衍生物，这是一类用于药物、增塑剂和各种其他添加剂的重要前体。
