Novel tartrate-based guanidines for enantioselective fluorination of 1,3-Dicarbonyl and α-cyano carbonyl compounds

Article abstract of DOI:10.1071/CH14179

A novel library of chiral guanidines featuring the tartaric acid skeleton is easily accessed with tunable steric and electronic properties. A guanidine molecule of this library with an incorporated 2,6-diisoaniline fragment was identified as a suitable promoter for the enantioselective fluorination of 1,3-dicarbonyl and α-cyano carbonyl compounds to furnish the fluorinated product with up to 84% ee and 99% yield using N-fluorobenzenesulfonimide (NFSI) as the fluorinating agent. CSIRO 2014.