CFTA, a new efficient agent for determination of absolute configurations of chiral secondary alcohols

Chemical Communications

Volumn , Issue 9, 2000, Pages 787-788

  Takahashi, Tamiko ^a   Fukuishima, Aki ^a   Tanaka, Yuki ^a   Takeuchi, Yoshio ^a   Kabuto, Kuninobu ^b   Kabuto, Chizuko ^b  

^a Med and Pharmaceutical University   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALCOHOL;

ARTICLE; CALCULATION; CHIRALITY; FLUORINATION; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY ANALYSIS;

EID: 0034616531     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001962n     Document Type: Article

References (23)

1. For reviews, see: (a) S. Yamaguchi, in Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 1983, vol. 1, p. 125;
2. (b) D. Parker, Chem. Rev., 1991, 91, 1441;
3. (c) Y. Takeuchi and T. Takahashi, in Enantiocontrolled Synthesis of Fluoro-organic Compounds, ed. V. A. Soloshonok, Wiley, Chichester, 1999, p. 497. For CDAs for determination of absolute configuration of chiral secondary alcohols:
4. (d) J. A. Dale and H. S. Mosher, J. Am. Chem. Soc., 1973, 95, 512;
5. (e) B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal and J. M. Balkovec, J. Org. Chem., 1986, 51, 2370;
6. (f) J. M. Seco, Sh. Latypov, E. Quiñoá and R. Riguera, Tetrahedron Lett., 1994, 35, 2921;
7. (g) I. Chataigner, J. Lebreton, D. Durand, A. Guingnant and J. Villiéras, Tetrahedron Lett., 1998, 39, 1759 and references therein.
8. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092; T. Kusumi, Synth. Org. Chem., 1993, 51, 462 and references therein.
9. I. Ohtani, T. Kusumi, Y. Kashman and H. Kakisawa, J. Am. Chem. Soc., 1991, 113, 4092; T. Kusumi, Synth. Org. Chem., 1993, 51, 462 and references therein.
10. H. Kawa, F. Yamaguchi and N. Ishikawa, J. Fluorine Chem., 1982, 20, 475; S. Hamman, J. Fluorine Chem., 1989, 45, 377; M. Barrele and S. Hamman, J. Chem. Res. (S), 1990, 100; 1995, 316.
11. H. Kawa, F. Yamaguchi and N. Ishikawa, J. Fluorine Chem., 1982, 20, 475; S. Hamman, J. Fluorine Chem., 1989, 45, 377; M. Barrele and S. Hamman, J. Chem. Res. (S), 1990, 100; 1995, 316.
12. H. Kawa, F. Yamaguchi and N. Ishikawa, J. Fluorine Chem., 1982, 20, 475; S. Hamman, J. Fluorine Chem., 1989, 45, 377; M. Barrele and S. Hamman, J. Chem. Res. (S), 1990, 100; 1995, 316.
13. H. Kawa, F. Yamaguchi and N. Ishikawa, J. Fluorine Chem., 1982, 20, 475; S. Hamman, J. Fluorine Chem., 1989, 45, 377; M. Barrele and S. Hamman, J. Chem. Res. (S), 1990, 100; 1995, 316.
14. Y. Takeuchi, N. Itoh, T. Satoh, T. Koizumi and K. Yamaguchi, J. Org. Chem., 1993, 58, 1812 and references therein.
15. Y. Takeuchi, M. Konishi, H. Hori, T. Takahashi, T. Kometani and K. L. Kirk, Chem. Commun., 1998, 365; Y. Takeuchi, M. Konishi, H. Hori, T. Takahashi and K. L. Kirk, Enantiomer, 1999, 4, 339.
16. Y. Takeuchi, M. Konishi, H. Hori, T. Takahashi, T. Kometani and K. L. Kirk, Chem. Commun., 1998, 365; Y. Takeuchi, M. Konishi, H. Hori, T. Takahashi and K. L. Kirk, Enantiomer, 1999, 4, 339.
17. 1f However, MPA chloride did not react with 10-bromoisoborneol.
18. N. Poth, Rev. Tech. Luxemb., 1976, 68, 195 (Chem. Abstr., 1977, 87, 135965k).
19. N. Poth, Rev. Tech. Luxemb., 1976, 68, 195 (Chem. Abstr., 1977, 87, 135965k).
20. The esters of (S)-acids with (R)-alcohols are designated SR and those of (R)-acids with (R)-alcohols are designated RR.
21. max = 0.22 e Å-3. At least one of the methyl hydrogens was located using a difference Fourier map and then the others were calculated geometrically on the basis of the observed hydrogen atoms. CCDC 182/1586. See http://www.rsc.org/suppdata/cc/b0/b001962n/ for crystallographic files in .cif format.
22. The tolyl group of CFTA was replaced by aphenyl group to reduce the number of atoms. The relative configuration of the (R, S) diastereomer is the same as that of the (S, R) diastereomer.
23. CFC13 = 0) - 128.59 (sp) and -145.33 (ap) for the (R, S) ester; -133.05 (sp) and -146.47 (ap) for the (R, R) ester.