Simple synthesis of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA) , a new efficient chiral derivatizing agent
Takeuchi, Y.; Konishi, M.; Hori, H.; Takahashi, T.; Kirk, K.L.
Enantiomer 4(3-4): 339-344
1999
ISSN/ISBN: 1024-2430 PMID: 10550891 Document Number: 500378
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.
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