Nucleophilic trifluoromethylation of cyclic imides using (trifluoromethyl)trimethylsilane CF3SiMe3.
A variety of cyclic five-membered imides was trifluoromethylated in good to excellent chemical yields using (trifluoromethyl)trimethylsilane CF3SiMe3 under fluoride ion catalysis. The method was successfully applied to the stereoselective synthesis of trifluoromethylated bi- and tricyclic lactams which could serve as precursors for designed thrombin inhibitors.
Laboratorium fur Organische Chemie, ETH-Honggerberg, CH-8093, Zurich, Switzerland.
Anja
A
Hoffmann-Röder
Paul
P
Seiler
François
F
Diederich
D003500:Cyclization; D005461:Fluorine / Q000737:chemistry*; D007094:Imides / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013917:Thrombin / Q000037:antagonists & inhibitors / Q000378:metabolism; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D007094:Imides; D014297:Trimethylsilyl Compounds; D005461:Fluorine; D013917:Thrombin