Structural aspects of nucleation inhibitors for diastereomeric resolutions and the relationship to Dutch resolution

Angewandte Chemie - International Edition

Volumn 47, Issue 7, 2008, Pages 1287-1290

  Leeman, Michel ^a   Brasile, Giuseppina ^a   Gelens, Edith ^a   Vries, Ton ^a   Kaptein, Bernard ^b   Kellogg, Richard ^a  

^a Syncom BV   (Netherlands)

^b Catalysis and Development   (Netherlands)

Author keywords

Chiral resolution; Crystal growth; Dutch resolution; Nucleation inhibitors; Phase diagrams

Indexed keywords

ACIDS; CHEMICAL REACTIONS;

CHIRAL RESOLUTION; CRYSTAL GROWTH; DUTCH RESOLUTION; NUCLEATION INHIBITORS; PHASE DIAGRAMS;

NUCLEATION;

ARTICLE; KINETICS; STEREOISOMERISM;

KINETICS; STEREOISOMERISM;

EID: 41249099537     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704021     Document Type: Article

References (27)

1. a) For the theory and practice of resolutions, see; J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Krieger, Malabar, FL, 1994;
2. b) See for example "Novel Optical Resolution Technologies": Topics in Current Chemistry (Eds.: K. Sakai, N. Hirayama, R. Tamura), Springer, Berlin, 2007.
3. T. Vries, H. Wynberg, E. van Echten, J. Koek, W. ten Hoeve, R. M. Kellogg, Q. B. Broxterman, A. Minnaard, B. Kaptein, S. van der Sluis, L. Hulshof, J. Kooistra, Angew. Chem. 1998, 110, 2491;
4. Angew. Chem. Int. Ed. 1998, 37, 2349.
5. In the sense of same relative absolute stereochemistries.
6. C. Gervais, R. F. P. Grimbergen, I. Markovits, G. J. A. Ariaans, B. Kaptein, A. Bruggink, Q. B. Broxterman, J. Am. Chem. Soc. 2004, 126, 655.
7. [1b] [6] a) J. W. Nieuwenhuijzen, R. F. P. Grimbergen, C. Koopman, R. M. Kellogg, T. R. Vries, K. Pouwer, E. van Echten, B. Kaptein, L. A. Hulshof, Q. B. Broxterman, Angew. Chem. 2002, 114, 4457;
8. Angew. Chem. Int. Ed. 2002, 41, 4281;
9. b) J. Dalmolen, T. D. Tiemersma-Wegman, J. W. Nieuwenhuijzen, M. van der Sluis, E. van Echten, T. R. Vries, B. Kaptein, Q. B. Broxterman, R. M. Kellogg, Chem. Eur. J. 2005, 11, 5619.
10. J. W. Mullins, Crystallization, 4th ed., Elsevier, Oxford, 2001, pp. 181-215.
11. L. Addadi, S. Weinstein, E. Gati, I. Weissbuch, M. Lahav, J. Am. Chem. Soc. 1982, 104, 4610.
12. Polymeric additives: a) I. Weissbuch, D. Zbaida, L. Addadi, L. Leiserowitz, M. Lahav, J. Am. Chem. Soc. 1987, 109, 1869;
13. b) Y. Mastai, M. Sedlák, H. Cölfen, M. Antonietti, Chem. Eur. J. 2002, 8, 2429.
14. Effects of trace impurities on amino acids: M. Lahav, I. Weissbuch, E. Shavit, C. Reiner, G. J. Nichols on, V. Schürig, Origins Life Evol. Biosphere 2006, 36, 151.
15. a) D. H. R. Barton, G. W. Kirby, J. Chem. Soc. 1962, 804;
16. b) see also: K. R. Wilson, R. E. Pincock, J. Am. Chem. Soc. 1975, 97, 1474.
17. Incorporation of a small amount of the inhibitor, perhaps in a polymorph formed at the beginning of precipitation of solid material, cannot be excluded.
18. See also: a) S. Kojo, E. Tanaka, Chem. Commun. 2001, 1980;
19. b) S. Kojo, H. Uchino, M. Yoshimura, K. Tanaka, Chem. Commun. 2004, 2146.
20. J. Dalmolen, M. van der Sluis, J. W. Nieuwenhuijzen, A. Meetsma, B. de Lange, B. Kaptein, R. M. Kellogg, Q. B. Broxterman, Eur. J. Org. Chem. 2004, 1544.
21. See reference [1a], p. 306.
22. Similar observations in other systems have been made: J. S. C. Loh, W. J. P. van Enckevort, E. Vlieg, C. Gervais, R. F. P. Grimbergen, B. Kaptein, Cryst. Growth Des. 2006, 6, 861.
23. In resolutions with 1% additive some of the additive is initially incorporated into the salt, but over a period of hours it slowly returns into solution.
24. [19] The resolution efficiency for racemate 1 is improved from S = 0.14 without the bifunctional additive 3 to S = 0.38 with 3% of additive 3. (Chemical Equation Presented)
25. R. M. Kellogg, J. W. Nieuwenhuijzen, K. Pouwer, T. R. Vries, Q. B. Broxterman, R. F. P. Grimbergen, B. Kaptein, R. M. La Crois, E. de Wever, K. Zwaagstra, A. C. van der Laan, Synthesis 2003, 1626.
26. D. W. Armstrong, J. T. Lee, L. W. Chang, Tetrahedron: Asymmetry 1998, 9, 2043.
27. E. Fogassy, A. Lopata, F. Faigl, F. Darvas, M. Ács, L. Toke, Tetrahedron Lett. 1980, 21, 647.