Cinchona alkaloids/TMAF combination-catalyzed nucleophilic enantioselective trifluoromethylation of aryl ketones.
The catalytic, nucleophilic enantioselective trifluoromethylation reaction of both acyclic and cyclic aryl ketones using the Ruppert-Prakash reagent is now at hand, with an operationally simple procedure, based on the combination of ammonium bromide of cinchona alkaloids with TMAF. The procedure is reliable and general. Trifluoromethyl-substituted tetrasubstituted aryl alcohols have been synthesized in up to 94% ee.
Mizuta
Satoshi
S
Department of Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Shibata
Norio
N
Akiti
Surendar
S
Fujimoto
Hiroyuki
H
Nakamura
Shuichi
S
Toru
Takeshi
T
D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D002930:Cinchona Alkaloids / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D007659:Ketones; D000644:Quaternary Ammonium Compounds; C027917:tetramethylammonium