Dutch resolution of racemic 4-hydroxy- and 4-fluorophenylglycine with mixtures of phenylglycine and (+)-10-camphorsulfonic acid

Tetrahedron Asymmetry

Volumn 11, Issue 6, 2000, Pages 1343-1351

  Kaptein, Bernard ^a   Elsenberg, Henk ^a   Grimbergen, Reinier F P ^a   Broxterman, Quirinus B ^a   Hulshof, Lumbertus A ^b   Pouwer, Kees L ^c   Vries, Ton R ^c  

^a DSM RESEARCH   (Netherlands)

^b DSM Fine Chemicals Austria Nfg GmbH & Co KG   (Netherlands)

^c Syncom BV   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CAMPHOR DERIVATIVE; PHENYLGLYCINE; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; OPTICAL RESOLUTION; PRIORITY JOURNAL; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0034616251     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00048-3     Document Type: Article

References (21)

1. Bruggink, A. In Chirality in Industry II; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; J. Wiley & Sons: Chichester, 1997; pp. 81-98.
2. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; Wiley Interscience: New York, 1981 (reissue: Krieger: Melbourne, F.L., 1994).
3. Collet, A. In Comprehensive Supramolecular Chemistry; Reinhoudt, D. N., Ed.; Elsevier Science: Amsterdam, 1996; pp. 113-149.
4. Collet, A. Angew. Chem. 1998, 37, 3239-3241.
5. See Ref. 2, pp. 392-294 and Ref. 3, pp. 135.
6. Valente, E. J.; Zubkowski, J.; Eggleston, D. S. Chirality 1992, 4, 494-504.
7. Constante, J.; Ehlinger, N.; Perrin, M.; Collet, A. Enantiomer 1996, 1, 377-386.
8. Vries, T.; Wynberg, H.; Van Echten, E.; Koek, J.; Ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A. J.; Kaptein, B.; Van der Sluis, S.; Hulshof, L.; Kooistra, J. Angew. Chem. 1998, 37, 2349-2354.
9. Broxterman, Q. B.; Van Echten, E.; Hulshof, L. A.; Kaptein, B.; Kellogg, R. M.; Minnaard, A. J.; Vries, T.; Wynberg, H. Chim. Oggi/Chem. Today 1998, 16, 34-37.
10. Kamphuis, J.; Boesten, W. H. J.; Kaptein, B.; Hermes, H. F. M.; Sonke, T.; Broxterman, Q. B.; Van Den Tweel, W. J. J.; Schoemaker, H. E. In Chirality in Industry; Collins, A. N.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley & Sons: Chichester, 1992; pp. 187-208.
11. Bruggink, A.; Roos, E. C.; De Vroom, E. Organic Process Research & Development 1998, 2, 128-133.
12. Alabaster, R. J.; Gibson, A. W.; Johnson, S. A.; Edwards, J. S.; Cottrell, I. F. Tetrahedron: Asymmetry 1997, 8, 447-450. Dorn, C. P.; Hale, J. J.; MacCoss, M.; Ladduwahetty, T.; Shah, S. K. Eur. Pat. Appl. 577394, 1994 (to Merck & Co.).
13. Alabaster, R. J.; Gibson, A. W.; Johnson, S. A.; Edwards, J. S.; Cottrell, I. F. Tetrahedron: Asymmetry 1997, 8, 447-450. Dorn, C. P.; Hale, J. J.; MacCoss, M.; Ladduwahetty, T.; Shah, S. K. Eur. Pat. Appl. 577394, 1994 (to Merck & Co.).
14. Moseley, J. D.; Williams, B. J.; Owen, S. N.; Verrier, H. M. Tetrahedron: Asymmetry 1996, 7, 3351-3352.
15. Mullin, J. W. Crystallization, 3rd ed.; Butterworth-Heinemann: Oxford, 1992; pp. 158-159. Roozenboom, H. W. B. Z. Phys. Chem. 1891, 8, 504.
16. Mullin, J. W. Crystallization, 3rd ed.; Butterworth-Heinemann: Oxford, 1992; pp. 158-159. Roozenboom, H. W. B. Z. Phys. Chem. 1891, 8, 504.
17. See Ref. 2, pp. 309-312.
18. Kitaigorodsky, A. I. Mixed Crystals; Springer-Verlag: Berlin, 1984.
19. Frega, A. Tetrahedron 1960, 8, 126-140.
20. See Ref. 3, pp. 142-143.
21. Garcia, C.; Collet, A. Tetrahedron: Asymmetry 1992, 3, 361-364.