Kinetic resolution of allyl fluorides by enantioselective allylic trifluoromethylation based on silicon-assisted C-F bond cleavage.
Two birds, one stone! The first kinetic resolution of allyl fluorides was achieved by the development of an organocatalyzed enantioselective allylic trifluoromethylation. Two kinds of chiral fluorinated compounds, which incorporate C*F and C*CF3 units, respectively, can thus be accessed by a single transformation.
Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555 (Japan).
Takayuki
T
Nishimine
Kazunobu
K
Fukushi
Naoyuki
N
Shibata
Hiromi
H
Taira
Etsuko
E
Tokunaga
Akihito
A
Yamano
Motoo
M
Shiro
Norio
N
Shibata
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008745:Methylation; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D006845:Hydrocarbons, Fluorinated; D017646:Organosilicon Compounds; D002244:Carbon; D005459:Fluorides
allyl fluorides; fluorine; kinetic resolution; organocatalysis; trifluoromethylation