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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
Author(s) -
Takahashi Tamiko,
Fukushima Aki,
Tanaka Yuki,
Segawa Masaru,
Hori Hitoshi,
Takeuchi Yoshio,
Burchardt Annegret,
Haufe Günter
Publication year - 2000
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(2000)12:5/6<458::aid-chir27>3.0.co;2-r
Subject(s) - chemistry , acetic acid , enantiomer , chiral derivatizing agent , enantiomeric excess , alcohol , ether , chiral column chromatography , stereochemistry , enantioselective synthesis , organic chemistry , medicinal chemistry , catalysis
The new chiral derivatizing agent (CDA), α‐cyano‐α‐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 α‐cyano(2‐naphthyl)acetate with FClO 3 . 2‐CFNA 1 has proven to be a significantly superior CDA for determination of enantiomeric excess (ee) of a primary alcohol when compared to α‐methoxy‐α‐trifluoromethylphenylacetic acid (MTPA, Mosher's agent) and α‐cyano‐α‐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 . Chirality 12:458–463, 2000. © 2000 Wiley‐Liss, Inc.