Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 60-72Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02316
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Funding
- NSFC [21632003, 21572087]
- key program of Gansu province [17ZD2GC011]
- 111 program from the MOE of P. R. China
- Syngenta Company
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Herein, we describe a novel and efficient method for constructing a series of fluorine-containing gamma-keto acid derivatives through combining visible-light photoredox catalysis and chiral Lewis acid catalysis. With this dual catalytic strategy, a variety of chiral gamma-keto amides containing a gem-difluoroalkyl group and a series of fluorine-containing alpha,beta-unsaturated-gamma-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 gamma-keto acid derivatives, an important class of precursors for pharmaceuticals, plasticizers, and various other additives.
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