New efficient chiral derivatizing agent, α-cyano-α-fluoro(2-naphthyl)acetic acid (2-CFNA). Application to the EE determination of (−)-3-acetoxy-2-fluoro-2-(hexadecyloxymethyl)propan-1-ol
✍ Scribed by Tamiko Takahashi; Aki Fukushima; Yuki Tanaka; Masaru Segawa; Hitoshi Hori; Yoshio Takeuchi; Annegret Burchardt; Günter Haufe
- Book ID
- 101297510
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 151 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0899-0042
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✦ Synopsis
The new chiral derivatizing agent (CDA), alpha-cyano-alpha-fluoro(2-naphthyl)-acetic acid (2-CFNA) 1 was prepared in optically pure form by chiral HPLC separation of racemic 2-CFNA methyl ester (2-CFNA Me ester) (+/-)-2. The ester was obtained by fluorination of methyl alpha-cyano(2-naphthyl)acetate with FClO3. 2-CFNA 1 has proven to be a significantly superior CDA for determination of enantiomeric excess (ee) of a primary alcohol when compared to alpha-methoxy-alpha-trifluoromethylphenylacetic acid (MTPA, Mosher's agent) and alpha-cyano-alpha-fluoro(p-tolyl)acetic acid (CFTA). The ee of (-)-3-acetoxy-2-fluoro-2-(hexadecyloxymethyl)propan-1-ol (-)-9, a fluorinated analog of anticancer active ether lipids, was determined using (+)-2-CFNA (+)-1.