Enantioselective fluorination of tert-butoxycarbonyl lactones and lactams catalyzed by chiral Pd(II)-bisphosphine complexes.
An efficient catalytic enantioselective fluorination of tert-butoxycarbonyl lactones and lactams is reported. Reactions of the lactone substrates proceeded smoothly in an alcoholic solvent with a catalytic amount of chiral Pd(II) complex. In the case of the less acidic lactam substrates, concurrent use of the Pd complex and 2,6-lutidine as a cocatalyst was effective. Under the reaction conditions, the fluorinated lactones and lactams were obtained in good yield with excellent enantioselectivity (94-99% ee).
Suzuki
Toshiaki
T
RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
Goto
Tomomi
T
Hamashima
Yoshitaka
Y
Sodeoka
Mikiko
M
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D007769:Lactams / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism
D000588:Amines; D007769:Lactams; D007783:Lactones; D010720:Phosphines; D005461:Fluorine; D010165:Palladium