Simple synthesis of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA), a new efficient chiral derivatizing agent

Authors
Takeuchi, Y Konishi, M Hori, H Takahashi, T Kirk, KL
Citation
Y. Takeuchi et al., Simple synthesis of alpha-cyano-alpha-fluoro-p-tolylacetic acid (CFTA), a new efficient chiral derivatizing agent, ENANTIOMER, 4(3-4), 1999, pp. 339-344
Citations number
15
Categorie Soggetti
Chemistry
Journal title
ENANTIOMER
ISSN journal
10242430 → ACNP
Volume
4
Issue
3-4
Year of publication
1999
Pages
339 - 344
Database
ISI
SICI code
1024-2430(1999)4:3-4<339:SSOAA(>2.0.ZU;2-9
Abstract
The new chiral derivatizing agent, alpha-cyano-alpha-fluoro-p-tolylacetic a cid (CFTA) (2) was prepared in optically pure form by Candida rugosa lipase (CRL)-mediated kinetic resolution of racemic CFTA ethyl ester (CFTA Et est er) (1). The eater was obtained by fluorination of ethyl alpha-cyano-p-toly lacetate with FClO3. The CFTA method has proven to be significantly superio r for enantiomeric excess (e.e.) determinations when compared to the MTPA m ethod, particularly in those compounds that have a remotely disposed chiral center.