Design, synthesis, and evaluation of a novel class of enantioselective electrophilic fluorinating agents: N-fluoro ammonium salts of cinchona alkaloids (F-CA-BF(4)).
The first enantiopure N-fluoro quaternary ammonium salts of cinchona alkaloids as enantioselective fluorinating agents are reported. A one-step transfer-fluorination on the naturally occurring cinchona alkaloids gave the fluorinating agents F-CA-BF(4). This new generation of fluorinating agents exhibited asymmetric induction up to 61% on fluorination of enolates and silyl enol ethers of 2-methyl-1-tetralone.
Cahard
D
D
UPRES-A 6014 de l'IRCOF (Institut de Recherche en Chimie Organique Fine), Université de Rouen, Rue Tesnière, F-76821 Mont Saint Aignan Cedex, France. dominique.cahard@univ-rouen.fr
Audouard
C
C
Plaquevent
J C
JC
Roques
N
N
D002930:Cinchona Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D005461:Fluorine; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D002930:Cinchona Alkaloids; D007202:Indicators and Reagents; D000644:Quaternary Ammonium Compounds; D005461:Fluorine