Synthesis and characterization of fluorous (S)- and (R)-1-phenylethylamines that effect heat facilitated resolution of (±)-2-(8-carboxy-1-naphthylsulfinyl)benzoic acid via diastereomeric salt formation and study of their circular dichroism

Journal of Fluorine Chemistry

Volumn 127, Issue 10 SPEC. ISS., 2006, Pages 1405-1414

  Szabó, Dénes ^a   Nemes, Anikó ^a   Kövesdi, István ^b   Farkas, Viktor ^a   Hollósi, Miklós ^a   Rábai, József ^a  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b EGIS PHARMACEUTICALS LTD   (Hungary)

Author keywords

Alkylation; Chiral amines; Circular dichroism; Fluorine; Fluorophilicity; Optical resolution; Specific rotation; Synthesis

Indexed keywords

EID: 33750343706     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.05.011     Document Type: Article

References (44)

1. Zhang W. Tetrahedron 59 (2003) 4475-4489
2. Werner S., and Curran D.P. Org. Lett. 5 (2003) 3293-3296
3. Dobbs A.P., and Kimberley M.R. J. Fluorine Chem. 118 (2002) 3-17
4. Lindsley C.W., and Leister W.H. In: Gladysz J.A., Curran D.P., and Horváth I.T. (Eds). Handbook of Fluorous Chemistry (2004), Wiley-VCH, Weinheim 236-246
5. Pozzi G., Cavazzini M., Quici S., Maillard D., and Sinou D. J. Mol. Catal. A 182-183 (2002) 455-461
6. Pozzi G., and Shepperson I. Coord. Chem. Rev. 242 (2003) 115-124
7. Shepperson I., Quici S., Pozzi G., Nicoletti M., and O'Hagan D. Eur. J. Org. Chem. (2004) 4545-4551
8. Bayardon J., Sinou D., Holcznecht O., Mercs L., and Pozzi G. Tetrahedron: Asymmetry 16 (2005) 2319-2327
9. Shepperson I., Cavazzini M., Pozzi G., and Quici S. J. Fluorine Chem. 125 (2004) 175-180
10. Kleijn H., Kleij A.W., de Pater J.J.M., Lutz M., Spek A., Jastrzebski J.T.B.H., Deelman B.-J., and van Koten G. Inorg. Chim. Acta 359 (2005) 2674-2682
11. Beletskaya I.P., and Cheprakov A.V. J. Organometal. Chem. 689 (2004) 4055-4082
12. Dupont J., Consorti C.S., and Spencer J. Chem. Rev. 105 (2005) 2527-2571
13. Fache F., and Piva O. Tetrahedron Lett. 42 (2001) 5655-5657
14. Jaques J., Collet A., and Wilen S.H. Enantiomers, Racemates, and Resolutions (1981), Wiley, New York pp. 251-368
15. In: Kozma D. (Ed). CRC Handbook of Optical Resolutions via Diastereomeric Salt Formation (2000), CRC Press, Boca Raton
16. Faigl F., and Kozma D. In: Toda F. (Ed). Enantiomer Separation: Fundamentals and Practical Methods (2004), Kluwer Academic Press, Dordrecht (Chapter 9)
17. Rocaboy C., Bauer W., and Gladysz J.A. Eur. J. Org. Chem. 14 (2000) 2621-2628
18. Szlávik Z., Tárkányi G., Gömöry A., Tarczay G., and Rábai J. J. Fluorine Chem. 108 (2001) 7-14
19. Rábai J., Abulikemu A., and Szabó D. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim (Chapter 11.27)
20. Abulikemu A., Halász G., Csámpai A., Gömöry A., and Rábai J. J. Fluorine Chem. 125 (2004) 1143-1146
21. Rábai J. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 156-174 (Chapter 9)
22. Bálint A.-M., Bodor A., Gömöry A., Vékey K., Szabó D., and Rábai J. J. Fluorine Chem. 126 (2005) 1524-1530
23. De Campo F., Lastécouères D., Vincent J.-M., and Verlhac J.-B. J. Org. Chem. 64 (1999) 4969-4971
24. Contel M., Izuel C., Laguna M., Villuendas P.R., Alonso P.J., and Fish R.H. Chem. Eur. J. 9 (2003) 4168-4178
25. Vincent J.-M., Lastécouères D., Contel M., Laguna M., and Fish R.H. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 298-305 (Chapter 10.12)
26. Vincent J.-M., and Fish R.H. In: Gladysz J.A., Horváth I.T., and Curran D.P. (Eds). Handbook of Fluorous Chemistry (2004), Wiley/VCH, Weinheim 393-394 (Chapter 11.14)
27. D. Szabó, J. Mohl, A.-M. Bálint, A. Bodor, J. Rábai, J. Fluorine Chem., in preparation.
28. Schmidt M., Amstutz R., Crass G., and Seebach D. Chem. Ber. 113 (1980) 1691-1707
29. de Wolf E., Ruelle P., van den Broeke J., Deelman B.-J., and van Koten G. J. Phys. Chem. B 108 (2004) 1458-1466
30. Szabó D., Bonto A.-M., Kövesdi I., Gömöry A., and Rábai J. J. Fluorine Chem. 126 (2005) 641-652
31. Rábai J. Angew. Chem. Int. Ed. Engl. 31 (1992) 1631-1633
32. Rábai J. Angew. Chem. 104 (1992) 1648-1650
33. Varga J., Rábai J., Ruff F., Kucsman A., Vass E., Hollósi M., and Szabó D. Tetrahedron: Asymmetry 14 (2003) 3745-3753
34. Fogassy E., Faigl F., and Ács M. Tetrahedron Lett. 22 (1981) 3093-3096
35. Fogassy E., Faigl F., and Ács M. Tetrahedron 41 (1985) 2841-2845
36. Ács M., Gizur T., Péter I., Harsányi K., Jászai Z.S., and Fogassy E. Mol. Cryst. Liq. Cryst. 187 (1990) 289-296
37. Fogassy E., Nógrádi M., Pálovics E., and Schindler J. Synthesis (2005) 1555-1568 (Review of the resolution of enantiomers by non-conventional methods)
38. Pope W.J., and Peachey S.J. J. Chem. Soc. 75 (1899) 1066-1093
39. Wilen S.H., Davidson R., Spector R., and Steffanou H. J. Chem. Soc. Chem. Commun. (1969) 603-604
40. Kantor S.W., and Hauser C.R. J. Am. Chem. Soc. 75 (1953) 1744
41. Johnson C.W., Fontana L.P., and Smith H.E. J. Am. Chem. Soc. 109 (1987) 3361-3366
42. Smith H.E. Chem. Rev. 98 (1998) 1709-1740
43. Smith H.E., and Willis T.C. J. Am. Chem. Soc. 93 (1971) 2282-2290
44. Katsuhara Y., Aramaki M., Ishii A., Kume T., Kawashima C., and Mitsumoto S. J. Fluorine Chem. 127 (2006) 8-17