Simple synthesis of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA), a new efficient chiral derivatizing agent.
The new chiral derivatizing agent, alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA) (2) was prepared in optically pure form by Candida rugosa lipase (CRL)-mediated kinetic resolution of racemic CFTA ethyl ester (CFTA Et ester) (1). The ester was obtained by fluorination of ethyl alpha-cyano-p-tolylacetate with FClO3. The CFTA method has proven to be significantly superior for enantiomeric excess (e.e.) determinations when compared to the MTPA method, particularly in those compounds that have a remotely disposed chiral center.
Takeuchi
Y
Y
Toyama Medical and Pharmaceutical University, Japan. takeuchi@ms.toyama-mpu.ac.jp
Konishi
M
M
Hori
H
H
Takahashi
T
T
Kirk
K L
KL
D000085:Acetates / Q000138:chemical synthesis*; D002175:Candida / Q000201:enzymology*; D002712:Chlorides / Q000737:chemistry; D007202:Indicators and Reagents / Q000138:chemical synthesis; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010648:Phenylacetates / Q000737:chemistry; D013237:Stereoisomerism; D014050:Toluene / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000085:Acetates; D002712:Chlorides; D007202:Indicators and Reagents; D010648:Phenylacetates; C101363:alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride; C401482:cyanofluoro-p-tolylacetic acid; D014050:Toluene; D008049:Lipase