An Overview of Cinchona Alkaloids in Chemistry

Cinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis

Volumn , Issue , 2009, Pages 1-10

  Song, Choong Eui ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

Asymmetric catalysis; Chirality; Cinchona alkaloids; Organocatalysts; Quinidine; Quinine

Indexed keywords

EID: 84865467981     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527628179.ch1     Document Type: Chapter

References (44)

1. Garfield, S. (2000) Mauve, Faber & Faber, London, p. 224.
2. From http://www.quinine-buchler.com/cinchona.htm.
3. Pasteur, L. (1853) Acad. Sci., 37, 162;
4. Pasteur, L. (1853) Liebigs Ann. Chem., 88, 209.
5. Newman, P. (1981) Optical Resolution Procedures for Chemical Compounds: Acids, vol. 2, Optical Resolution Information Center, Manhattan College, Riverdale, NY, pp. 7-22;
6. Jacques, J., Collet, A., and Wilen, S.H. (1981) Enantiomers, Racemates and Resolutions, John Wiley & Sons, Inc., New York, pp. 254, 257;
7. Sheldon, R.A. (1993) Chirotechnology, Marcel Dekker, NewYork, Chapter 6;
8. Kozma, D. (2002) CRC Handbook of Optical Resolutions via Diastereomeric Salts, CRC Press, Boca Raton, FL.
9. Excellent reviews about quinine total synthesis with historical background: Kaufmann, T.S. and Rúveda, E.A. (2005) Angew. Chem. Int. Ed., 44, 854;
10. Weinreb, S.M. (2001) Nature, 411, 429;
11. Nicolaou, K.C. and Sorensen, E.J. (1996) in Classics in Total Synthesis: Targets, Strategies, Methods, Wiley-VCH Verlag GmbH, Weinheim, Chapter 15.
12. Bredig, G. and Fiske, P.S. (1912) Biochem. Z., 46, 7;
13. Bredig, G. and Minaeff, M. (1932) Biochem. Z., 249, 241.
14. Pracejus, H. (1960) Justus Liebigs Ann. Chem., 634, 9;
15. Pracejus, H. and Matje, H. (1964) J. Prakt. Chem., 24, 195.
16. Wynberg, H. (1986) Top. Stereochem., 16, 87.
17. Selected reviews: Kolb, H.C., Van Nieuwenhze, M.S., and Sharpless, K.B. (1994) Chem. Rev., 94, 2483;
18. Kolb, H.C. and Sharpless, K.B. (1998) in Transition Metals for Organic Synthesis, vol. 2 (eds M. Beller and C. Bolm), Wiley-VCH Verlag GmbH, Weinheim, p. 219;
19. Johnson, R.A. and Sharpless, K.B. (2000) in Catalytic Asymmetric Synthesis, 2nd edn (ed. I. S Ojima), John Wiley & Sons, Inc., New York, p. 357;
20. Beller, M. and Sharpless, K.B. (2002) in Applied Homogeneous Catalysis with Organometallic Compounds, 2nd edn, vol. 3 (eds B.H. Cornils and A. Wolfgang), Wiley-VCH Verlag GmbH, Weinheim, p. 1149.
21. Berkessel, A. and Gröger, H. (2005) Asymmetric Organocatalysis, Wiley-VCH Verlag GmbH, Weinheim;
22. Dalko, P.I. (ed.) (2007) Enantioselective Organocatalysis, Wiley-VCH Verlag GmbH, Weinheim;
23. List, B. (ed.) (2007) Chem. Rev., 107, 5413 (special issue on organocatalysis);
24. Houk, K.N. and List, B. (eds) (2004) Acc. Chem. Res., 37, 487 (special issue on asymmetric organocatalysis).
25. Berrisford, D.J., Bolm, C., and Sharpless, K.B. (1995) Angew. Chem. Int. Ed., 34, 1059.
26. For recent reviews on asymmetric phase-transfer catalysis, see Maruoka, K. (ed.) (2008) Asymmetric Phase Transfer Catalysis, Wiley-VCH Verlag GmbH, Weinheim;
27. Hashimoto, T. and Maruoka, K. (2007) Chem. Rev., 107, 5656.
28. For a recent review on organocatalysis via hydrogen bonding, see Doyle, A.G. and Jacobsen, E.N. (2007) Chem. Rev., 107. 5713.
29. For a recent review on enamine catalysis, see Mukherjee, S., Yang, J.W., Hoffmann, S., and List, B. (2007) Chem. Rev., 107. 5471.
30. For a recent review on iminium catalysis, see Erkkilä, A., Majander, I., and Pihko, P.M. (2007) Chem. Rev., 107. 5416.
31. Dijkstra, G.D.H., Kellogg, R.M., and Wynberg, H. (1989) Recl. Trav. Chim. Pays-Bas, 108, 195;
32. Dijkstra, G.D.H., Kellogg, R.M., Wynberg, H., Svendsen, J.S., Marko, I., and Sharpless, K.B. (1989) J. Am. Chem. Soc., 111, 8069.
33. Dijkstra, G.D.H., Kellogg, R.M., and Wynberg, H. (1990) J. Org. Chem., 55, 6121.
34. Burgi, T. and Baiker, A. (1998) J. Am. Chem. Soc., 120, 12920.
35. Olsen, R.A., Borchardt, D., Mink, L., Agarwal, A., Mueller, L.J., and Zaera, F. (2006) J. Am. Chem. Soc., 128, 15594.
36. Aune, M., Gogoll, A., and Matsson, O. (1995) J. Org. Chem., 60, 1356.
37. Maier, N.M., Schefzick, S., Lombardo, G.M., Feliz, M., Rissanen, K., Lindner, W., and Lipkowitz, K.B. (2002) J. Am. Chem. Soc., 124, 8611.
38. Hiemstra, H. and Wynberg, H. (1981) J. Am. Chem. Soc., 103, 417.
39. Rho, H.S., Oh, S.H., Lee, J.W., Lee, J.Y., Chin, J., and Song, C.E. (2008) Chem. Commun., 1208.
40. Williams, T., Pitcher, R.G., Bommer, P., Gutzwiller, J., and Uskokovic, M. (1969) J. Am. Chem. Soc., 91, 1871.
41. Uccello-Barretta, G., Bari, L.D., and Salvadori, P. (1992) Magn. Reson. Chem., 30, 1054.
42. Marchettini, N., Valensin, G., and Gaggelli, E. (1990) Biophys. Chem., 36, 65.
43. Casabianca, L.B. and de Dios, A.C. (2004) J. Phys. Chem. A, 108, 8505.
44. Tárkányi, G., Kiraly, P., Varga, S., Vakulya, B., and Soós, T. (2008) Chem. Eur.J., 14, 6078.