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

Chirality

Volumn 12, Issue 5-6, 2000, Pages 458-463

  Takahashi, Tamiko ^a   Fukushima, Aki ^a   Tanaka, Yuki ^a   Segawa, Masaru ^a   Hori, Hitoshi ^a   Takeuchi, Yoshio ^a   Burchardt, Annegret ^b   Haufe, Günter ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

( ) 3 acetoxy 2 fluoro 2 (hexadecyloxymethyl)propan 1 ol; Chiral derivatizing agent; Ee determination; HPLC; cyano fluoro(2 naphthyl)acetic acid; (F)

Indexed keywords

3 ACETOXY 2 FLUORO 2 (HEXADECYLOXYMETHYL)PROPAN 1 OL; ACETIC ACID DERIVATIVE; ALPHA CYANO ALPHA FLUORO(2 NAPHTHYL)ACETIC ACID; PROPANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; CONTROLLED STUDY; DERIVATIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034128190     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-636x(2000)12:5/6<458::aid-chir27>3.0.co;2-r     Document Type: Article

References (22)

1. Takeuchi Y, Takahashi T. Fluorine-containing agents for determining enantiomeric excess of chiral molecules. In: Soloshonok VA, editor. Enantiocontrolled synthesis of fluoro-organic compounds. Chichester: John Wiley & Sons; 1999. p 497-534.
2. 19F NMR Δδ values. J Am Chem Soc 1991;113:6318-6320.
3. 19F NMR Δδ values in enantiomeric excess determination. J Org Chem 1993;58:1812-1820 and references therein.
4. (a) Takeuchi Y, Konishi M, Hori H, Takahashi T, Kometani T, Kirk KL. Efficient synthesis of a new, highly versatile CDA, α-cyano-α-fluoro-p-tolylacetic acid (CFTA). Chem Commun 1998;365-366.
5. (b) Takeuchi Y, Konishi M, Hori H, Takahashi T, Kirk KL. Simple synthesis of α-cyano-α-fluoro-p-tolylacetic acid (CFTA), a new efficient chiral derivatizing agent. Enantiomer 1999;4:339-344.
6. Takeuchi Y, Murayama A, Hagi T, Koizumi T. Chemistry of the multifunctional carbon compounds. II. Synthesis of some α-fluoro-α-nitro-α-(arylthio)acetic esters. Nippon Kagaku Kaishi 1985;10:2029-2033. Chem Abstr 1986;105:42312v.
7. Takeuchi Y, Murayama A, Hagi T, Koizumi T. Chemistry of the multifunctional carbon compounds. II. Synthesis of some α-fluoro-α-nitro-α-(arylthio)acetic esters. Nippon Kagaku Kaishi 1985;10:2029-2033. Chem Abstr 1986;105:42312v.
8. Takeuchi Y, Iwashita H, Yamada K, Gotaishi M, Kurose N, Koizumi T, Kabuto K, Kometani T. Chemistry of novel compounds possessing multifunctional carbon atoms. X. Synthetic studies of efficient and practical chiral derivatizing agents based on the α-cyano-α-fluorophenylacetic acid structure. Chem Pharm Bull 1995;43:1668-1673.
9. Burchardt A, PhD Thesis, University of Münster, 1998.
10. 19F chemical shifts of α-methoxy-α-trifluoromethylphenylacetate derivatives. J Org Chem 1973;38:2143-2147.
11. Goj O, Burchardt A, Haufe G. A versatile approach to optically active primary 2-fluoro-2-phenylalkanols through lipase-catalyzed transformations. Tetrahedron: Asymmetry 1997;8:399-408.
12. (a) Kitazume T, Asai M, Un JT, Yamazaki T. The synthesis of optically active building blocks carrying a monofluoromethyl group. J Fluorine Chem 1987;35:477-488.
13. (b) Yamazaki T, Ichikawa S, Kiazume T. Diastereo-as well as enantioselective lipase-catalyzed asymmetric hydrolysis of chlorofluoromethylated alcohols. J Chem Soc Chem Commun. 1989:253-255.
14. (c) Kazlauskas RJ, Weissfloch ANE, Rappaport AT, Cuccia LA. A rule to predict which enantiomer of a secondary alcohol reacts faster in reactions catalyzed by cholesterol esterase, lipase from Pseudomonas cepacia, and lipase from Candida rugosa. J Org Chem 1991;56:2656-2665 and references therein.
15. (d) Sattler A, Haufe G. Synthesis of (9R)- and (9S)-10-fluorodecan-9-olide (fluoro-phoracantholide I). First lipase-catalyzed enantioselective esterification of β-fluoroalcohols. Tetrahedron: Asymmetry 1995;6:2841-2848.
16. (a) Ehrler J, Seebach D. Enantioselektive Verseifungen substituierter, achiraler 3-Acetoxy-propylester mit Lipasen: Herstellung chiraler Derivate von "Tris(hydroxymethyl)-methan." Liebigs Ann Chem 1990: 379-388.
17. (b) Guanti G, Banfi L, Narisano E. Chemoenzymatic preparation of asymmetrized tris(hydroxymethyl)methane (THYM)* and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA)* as new highly versatile chiral building blocks. J Org Chem 1992;57:1540-1554.
18. (c) Alexandre F-R, Huet F. Asymmetrization of meso-1,3-diols utilizing Pseudomonas fluorescens lipase. Tetrahedron: Asymmetry 1998;9:2301-2310.
19. 19F NMR spectra. When (S)-(+)-methoxymandelic acid was used a small shift-difference was found, but the signals were not baseline separated.
20. Parker D. NMR determination of enantiomeric purity. Chem Rev 1991; 91:1441-1457.
21. 1H NMR; see: (a) Seco JM, Latypov SH, Quinoa E, Riguera R. New chirality recognizing reagents for the determination of absolute stereochemistry and enantiomeric purity by NMR. Tetrahedron Lett 1994;35:2921-2924.
22. (b) Kusumi T, Takahashi H, Xu P, Fukushima T, Asakawa Y, Hashimoto T, Kan Y, Inouye Y. New chiral anisotropic reagents, NMR tools to elucidate the absolute configurations of long-chain organic compounds. Tetrahedron Lett 1994;35:4397-4400.