title: New efficient chiral derivatizing agent, alpha-cyano-alpha-fluoro(2-naphthyl)acetic acid (2-CFNA). application to the EE determination of (-)-3-acetoxy-2-fluoro-2-(hexadecyloxymethyl)propan-1-ol.
abstract: 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.
authors.affiliation: Toyama Medical & Pharmaceutical University, Toyama, Japan. takeuchi@ms.toyama-mpu.ac.jp
authors.forename: T
authors.initials: T
authors.lastname: Takahashi
authors.forename: A
authors.initials: A
authors.lastname: Fukushima
authors.forename: Y
authors.initials: Y
authors.lastname: Tanaka
authors.forename: M
authors.initials: M
authors.lastname: Segawa
authors.forename: H
authors.initials: H
authors.lastname: Hori
authors.forename: Y
authors.initials: Y
authors.lastname: Takeuchi
authors.forename: A
authors.initials: A
authors.lastname: Burchardt
authors.forename: G
authors.initials: G
authors.lastname: Haufe