Separation and purification of enantiomers by crystallisation methods

Enantiomer

Volumn 4, Issue 3-4, 1999, Pages 157-172

  Collet, André ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

Crystallisation; Diastereoisomers; Enantiomers; Phase diagrams; Racemates; Resolution

Indexed keywords

AGRICULTURAL CHEMICAL; DELTAMETHRIN; MENTHOL; NAPROXEN; PHENYLGLYCINE;

ANALYTIC METHOD; CHEMICAL INDUSTRY; CONFERENCE PAPER; CRYSTALLIZATION; DRUG MANUFACTURE; ENANTIOMER; PRIORITY JOURNAL; PURIFICATION; RACEMIC MIXTURE;

EID: 0032717776     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (51)

1. E.L. Eliel, S.H. Wilen and N. Mander, Stereochemistry of Organic Compounds, John Wiley & Sons, New York, 1994.
2. L. Pasteur, C. R. Acad. Sci., 1848, 26, 535.
3. L. Pasteur, C. R. Acad. Sci., 1853, 37, 162.
4. H. Leuchs and J. Wutke, Ber., 1913, 46, 2420.
5. A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry, Wiley, 1994.
6. Ibid. Chirality in Industry II, 1997.
7. S. Ahuja (Ed.), Chiral Separations, Applications and Technology, American Chemical Society, Washington DC, 1997.
8. R. Hopp, in R. Hopp and K. Mori (Eds.), Recent Developments in Flavor and Fragrance Chemistry, VCH, Weinheim, 1993, p. 13.
9. P.J. Harrington and E. Lodewijk, Organic Process Research & Development, 1997, 1, 72.
10. D.F. Reinhold, R.A. Firestone, W.A. Gaines, J.M. Chemerda and M. Sletzinger, J. Org. Chem., 1968, 33, 1209.
11. J. Kamphuis, W.H.J. Boesten, B. Kaptein, H.F.M. Hermes, T. Sonke, Q.B. Broxterman, W.J.J. van den Tweel and H.E. Schoemaker, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry, Wiley, New York, 1994, p. 189. The classical resolution of phenylglycine by camphorsulfonic acid has recently been discontinued (1999); DSM now produces the D-isomer by enzymatic resolution.
12. Roussel-Uclaf, Brevet Français, 76, 12094, 1976;
13. Brevet Français, ibid. 77 06099, 1977.
14. See also J. Martel, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry, Wiley, New York, 1994, p. 87.
15. J. Jacques, A. Collet and S.H. Wilen, Enantiomers, Racemates, and Resolutions, John Wiley & Sons, New York, 1981.
16. Ibid. Reissue with Corrections, Krieger, Malabar, Florida 1994.
17. A. Collet in D.N. Reinhoudt (Ed.), Comprehensive Supramolecular Chemistry, Vol. 10, Pergamon, Oxford, 1996, Chapter 5, p. 113.
18. A. Collet, L. Ziminski, C. Garcia and F. Vigné-Maeder, in J.S. Siegel (Ed.), Supramolecular Stereochemistry, NATO ASI Series: Kluwer, Dordrecht, 1995, p. 91.
19. For relevant examples see: B. Chion, J. Lajzerowicz, D. Bordeaux, A. Collet and J. Jacques, J. Phys. Chem., 1978, 82, 2682.
20. See Ref. 12, p. 183 and: G.A. Potter, C. Garcia, R. McCague, B. Adger and A. Collet, Angew. Chem., Intern. Edn., 1996, 35, 1666.
21. J. Gabard and A. Collet, Nouv. J. Chim., 1986, 10, 685.
22. W.P. Shum and M.J. Cannarsa, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry II, Wiley, New York, 1997, p. 363 (see p. 373).
23. D. Seebach, P. Renaud, W.B. Schweizer, M. Züger and M.-J. Brienne, Helv. Chim. Acta, 1984, 67, 1843.
24. S.C. Stinson, Chem. Eng. News, 1994 (September 19), p. 38.
25. A. Collet, M.-J. Brienne and J. Jacques, Chem. Rev., 1980, 80, 215.
26. See: S.C. Stinson, Chem. Eng. News, 1993 (September 27), p. 38.
27. W.M.L. Wood, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry II, Wiley, New York, 1997, p. 119.
28. L. Velluz, G. Amiard and R. Joly, Bull. Soc. Chim. France, 1953, 342.
29. L. Coppi, G. Giordano, A. Longoni and S. Panossian, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry II, Wiley, New York, 1997, p. 353. Parke, Davis and Co., US Pat. 2 767 213, 1952.
30. H.H. Jensen, Ger. Offen., 1 807 495, 1970. See ref. 12, p. 241.
31. F. Toda, in D.D. MacNicol, F. Toda and R. Bishop (Eds.), Comprehensive Supramolecular Chemistry, Vol. 6, Pergamon, Oxford, 1996, p. 465.
32. K. Tanaka and F. Toda, Comprehensive Supramolecular Chemistry, ibid., p. 517.
33. E. Weber, in D.D. MacNicol, F. Toda and R. Bishop (Eds.), Comprehensive Supramolecular Chemistry, Vol. 6, Pergamon, Oxford, 1996, p. 535.
34. J. Costante, N. Ehlinger, M. Perrin and A. Collet, Enantiomer, 1996, 1, 377.
35. J. Costante, L. Hecht, P.L. Polaravapu, A. Collet and L. Barron, Angew. Chem. Int. Edn., 1997, 36, 885.
36. Angew. Chem., 1997, 109, 917.
37. K. Kinbara, K. Sakai, Y. Hashimoto, H. Nohira and K. Saigo, Tetrahedron Asym., 1996, 7, 1539.
38. A. Collet, in A.M. Krstulovic (Ed.), Chiral separations by HPLC, Ellis Horwood Ltd, Chichester, 1989, p. 81.
39. T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R.M. Kellogg, R. Broxterman, A. Minaard, B. Kaptein, S. van der Sluis, L. Hulshof and J. Kooistra, Angew. Chem. Int. Ed., 1998, 37, 2349.
40. Angew. Chem., 1998, 110, 2491.
41. S. Stinson, Chem. Eng. News, 1998 (May 25), p. 9.
42. A. Collet, Angew. Chem. Int. Ed., 1998, 37, 3239.
43. Angew. Chem., 1998, 110, 3429.
44. L.A. Hulshof, Q.B. Broxterman, T.R. Vries, H. Wijnberg and E. van Echten (DSM N.V.), EP 0 838 448 A1, 1997.
45. S. Yamada, C. Hongo and R. Yoshioka, J. Org. Chem., 1983, 48, 843.
46. C. Hongo, M. Tohyama, R. Yoshioka, S. Yamada and I. Chibata, Bull. Chem. Soc. Japan, 1985, 58, 433.
47. C. Hongo, S. Yamada and I. Chibata, Bull. Chem. Soc. Japan, 1981, 54, 3291.
48. S.N. Black, L.J. Williams, R.J. Davey, F. Moffat, R.V.H. Jones, D.M. McEwan and D.E. Sadler, Tetrahedron, 1989, 45, 2677.
49. S. Sifniades, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry, Wiley, New York, 1994, p. 79.
50. A. Bruggink, in A.N. Collins, G.N. Sheldrake and J. Crosby (Eds.), Chirality in Industry II, Wiley, New York, 1997, p. 81.
51. A. Collet and F. Vigné-Maeder, New. J. Chem., 1995, 19, 877.