Synthesis of medicinally interesting polyfluoro ketones via perfluoroalkyl lithium reagents.
The addition of (pentafluoroethyl)- and (heptafluoropropyl)lithium to various acyl derivatives was studied. Weinreb and morpholine amides led to polyfluoro ketones in high to quantitative yields in short reaction times. Derivatives of 2-fluorocarboxylic acids may produce 1,1,1,2,2,4-hexafluoro ketones and 1,1,1,2,2,3,3,5-octafluoro ketones. The methodology can provide inhibitors for various lipolytic enzymes, including phospholipase A2.
Kokotos
Christoforos G
CG
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens 15771, Greece.
Baskakis
Constantinos
C
Kokotos
George
G
D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D005466:Fluorocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis*; D018020:Lithium Compounds / Q000737:chemistry*; D008722:Methods; D010740:Phospholipases / Q000037:antagonists & inhibitors
D004791:Enzyme Inhibitors; D005466:Fluorocarbons; D007202:Indicators and Reagents; D007659:Ketones; D018020:Lithium Compounds; D010740:Phospholipases