Dutch Resolution: Separation of enantiomers with families of resolving agents. A status report

Synthesis

Volumn , Issue 10, 2003, Pages 1626-1638

  Kellogg, Richard M ^a   Nieuwenhuijzen, José W ^a   Pouwer, K ^a   Vries, Ton R ^a   Broxterman, Quirinus B ^b   Grimbergen, Reinier F P ^c   Kaptein, Bernard ^b   La Crois, René M ^a   De Wever, Ellen ^a   Zwaagstra, Karen ^a   Van Der Laan, Alexander C ^a  

^a Syncom BV   (Netherlands)

^b DSM RESEARCH   (Netherlands)

^c NONE

Author keywords

Amino alcohols; Asymmetric synthesis; Camphor; Chalcones; Chiral auxiliaries; Chiral resolution; Chirality; Sulfonic acids

Indexed keywords

CHEMICAL ENGINEERING; ISOMERS; MIXTURES;

ENANTIOMERS;

SYNTHESIS (CHEMICAL);

ALCOHOL; CAMPHOR; CHALCONE; PHOSPHORIC ACID DERIVATIVE; SULFONIC ACID DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHIRALITY; DUTCH RESOLUTION; ENANTIOMER; NETHERLANDS; NOMENCLATURE; RACEMIC MIXTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0042745453     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40508     Document Type: Article

References (54)

1. Rouhi, M. Chem. Eng. News 2002, 80(23), 43.
2. (a) Sheldon, R. A. Chirotechnology, Chap. 6; Marcel Dekker: New York, 1993.
3. (b) Chirality in Industry II; Collins, N. A.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1997.
4. (a) Vries, T.; Wynberg, H.; van Echten, E.; Koek, J.; ten Hoeve, W.; Kellogg, R. M.; Broxterman, Q. B.; Minnaard, A.; Kaptein, B.; van der Sluis, S.; Hulshof, L. A.; Kooistra, J. Angew. Chem. Int. Ed. 1998, 37, 2349.
5. (b) See also: Broxterman, Q. B.; van Echten, E.; Hulshof, L. A.; Kaptein, B.; Kellogg, R. M.; Minnaard, A. J.; Vries, T. R.; Wynberg, H. Chem. Today 1998, 129, 4278.
6. Jacques, J. Collet, A. Wilen, S. H. Enantiomers, Racemates and Resolutions; Wiley: New York, 1981.
7. For a broad overview see: Noyori, R. Angew. Chem. Int. Ed. 2002, 41, 2008.
8. Excellent books and chapters on resolution phenomena are: (a) Kozma, D. Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, 2002. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Chap. 7; Wiley-Interscience: New York, 1994. (c) See also 2a (d) Wilen, S. H. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry; Wiley-Interscience: New York, 1971, Vol. 6. (e) Wilen, S. H. Tables of Resolving Agents and Optical; Eliel, E. L., Ed.; University of Notre Dame Press: London, 1972. (f) Newman, P. Optical Resolutions Procedures for Chemical Compounds; Optical Resolution Information Centre: New York, 1971.
9. Excellent books and chapters on resolution phenomena are: (a) Kozma, D. Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, 2002. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Chap. 7; Wiley-Interscience: New York, 1994. (c) See also 2a (d) Wilen, S. H. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry; Wiley-Interscience: New York, 1971, Vol. 6. (e) Wilen, S. H. Tables of Resolving Agents and Optical; Eliel, E. L., Ed.; University of Notre Dame Press: London, 1972. (f) Newman, P. Optical Resolutions Procedures for Chemical Compounds; Optical Resolution Information Centre: New York, 1971.
10. Excellent books and chapters on resolution phenomena are: (a) Kozma, D. Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, 2002. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Chap. 7; Wiley-Interscience: New York, 1994. (c) See also 2a (d) Wilen, S. H. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry; Wiley-Interscience: New York, 1971, Vol. 6. (e) Wilen, S. H. Tables of Resolving Agents and Optical; Eliel, E. L., Ed.; University of Notre Dame Press: London, 1972. (f) Newman, P. Optical Resolutions Procedures for Chemical Compounds; Optical Resolution Information Centre: New York, 1971.
11. Excellent books and chapters on resolution phenomena are: (a) Kozma, D. Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, 2002. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Chap. 7; Wiley-Interscience: New York, 1994. (c) See also 2a (d) Wilen, S. H. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry; Wiley-Interscience: New York, 1971, Vol. 6. (e) Wilen, S. H. Tables of Resolving Agents and Optical; Eliel, E. L., Ed.; University of Notre Dame Press: London, 1972. (f) Newman, P. Optical Resolutions Procedures for Chemical Compounds; Optical Resolution Information Centre: New York, 1971.
12. Excellent books and chapters on resolution phenomena are: (a) Kozma, D. Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, 2002. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Chap. 7; Wiley-Interscience: New York, 1994. (c) See also 2a (d) Wilen, S. H. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry; Wiley-Interscience: New York, 1971, Vol. 6. (e) Wilen, S. H. Tables of Resolving Agents and Optical; Eliel, E. L., Ed.; University of Notre Dame Press: London, 1972. (f) Newman, P. Optical Resolutions Procedures for Chemical Compounds; Optical Resolution Information Centre: New York, 1971.
13. Excellent books and chapters on resolution phenomena are: (a) Kozma, D. Handbook of Optical Resolutions via Diastereomeric Salt Formation; CRC Press: Boca Raton, 2002. (b) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds, Chap. 7; Wiley-Interscience: New York, 1994. (c) See also 2a (d) Wilen, S. H. Resolving Agents and Resolutions in Organic Chemistry In Topics in Stereochemistry; Wiley-Interscience: New York, 1971, Vol. 6. (e) Wilen, S. H. Tables of Resolving Agents and Optical; Eliel, E. L., Ed.; University of Notre Dame Press: London, 1972. (f) Newman, P. Optical Resolutions Procedures for Chemical Compounds; Optical Resolution Information Centre: New York, 1971.
14. (a) ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508.
15. (b) ten Hoeve, W.; Wynberg, H. Eur. Pat. 180,276 1989; US Pat. 4,814,477, 1989.
16. Gizur, T.; Péteri, I.; Harsányi, K.; Fogassy, E. Tetrahedron: Asymmetry 1996, 7, 1589.
17. Nieuwenhuijzen, J. W.; Grimbergen, R. F. P.; Koopman, C.; Kellogg, R. M.; Vries, T. R.; Pouwer, K.; van Echten, E.; Kaptein, B.; Hulshof, L. A.; Broxterman, Q. B. Angew. Chem. Int. Ed. 2002, 41, 4281.
18. (a) Bouillon, D.; Vayssie, C.; Richard, F. US Patent 4,304,730, 1981;.
19. (b) Bouillon, D.; Vayssie, C.; Richard, F. US Patent 4,330488, 1982;.
20. (c) Bouillon C., Vayssie C., Richard F. US Patent 4,323,549, 1982; and further patents cited; for some other sulfonic acid derivatives see:.
21. (d) Boesten, W. H. J. US Patent 4,111,980, 1978;.
22. (e) Bruggink, A.; Roos, E. C.; De Vroom, E. Org. Process Res. Dev. 1998, 2, 128.
23. (a) Evans, E. B.; Mabbott, E. E.; Turner, E. E. J. Chem. Soc. 1927, 1159.
24. (b) Anderson, A. R.; Short, W. F. J. Chem. Soc. 1933, 485.
25. (c) Agami, C.; Prince, B.; Puchot, C. Synth. Commun. 1990, 20, 3289.
26. (d) Ashworth, F.; Burkhardt, G. N. J. Chem. Soc. 1928, 1791.
27. (e) for a review on sulfonations see: Gilbert, E. E. Synthesis 1969, 1, 3.
28. (a) Corey, E. J.; Cimprich, K. A. Tetrahedron Lett. 1992, 33, 4099.
29. (b) Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551.
30. (c) Corey, E. J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988, 53, 2861.
31. (d) Corey, E. J.; Bakshi, R. K. Tetrahedron Lett. 1990, 31, 611.
32. (a) Yoshioka, R.; Tohyama, M.; Ohtsuki, O.; Yamada, S.; Chibata, I. Bull. Chem. Soc. Jpn. 1987, 60, 649.
33. (b) Yoshioka, R.; Ohtsuki, O.; Senuma, M.; Tosa, T. Chem. Pharm. Bull. 1989, 37, 883.
34. (c) Yoshioka, R.; Ohtsuki, O.; Da-Te, T.; Okamura, K.; Senuma, M. Bull. Chem. Soc. Jpn. 1994, 67, 3012.
35. (d) Yoshioka, R.; Okamura, K.; Yamada, S.; Aoe, K.; Da-Te, T. Bull. Chem. Soc. Jpn. 1998, 71, 1109.
36. Knoevenagel, E. Berichte 1904, 31, 4038.
37. Pfoertner, K. H. Helv. Chim. Acta 1980, 63, 664.
38. (a) Dahlman, O.; Månson, K. J. Wood Chem. Technol. 1996, 16, 47.
39. (b) Richtzenhain, H.; Alfredsson, B. Berichte 1956, 89, 378.
40. (c) Richtzenhain, H. Berichte 1939, 72, 2152.
41. (d) Kratzl, K.; Däubner, H. Monatsh. Chem. 1948, 78, 376.
42. (e) Browne, M. F.; Shriner, R. L. J. Org. Chem. 1957, 22, 1320.
43. (f) Kratzl, D.; Däubner, H. Berichte 1944/1946, 77/79, 519.
44. (a) Chirality in Industry. II; Collins, N. A.; Sheldrake, G. N.; Crosby, J., Eds.; Wiley: Chichester, 1997, 101.
45. (b) Watanabe, M.; Murata, K.; Ikariya, T. J. Org. Chem. 2002, 67, 1712.
46. Van der Sluis, M.; Dalmolen, J.; de Lange, B.; Kaptein, B.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 3943.
47. Dalmolen, J. Eur. J. Org. Chem. to be submitted.
48. Fogassy, E.; Lopata, A.; Faigl, F.; Darvas, F.; Ács, M.; Toke, L. Tetrahedron Lett. 1980, 21, 647.
49. Pope, W. J., Peachy, S. J. J. Chem. Soc. 1899, 5, 1066.
50. Kaptein, B. et al. manuscript in preparation.
51. Kohler, E. P.; Chadwell, H. M. Org. Synth., Coll. Vol. I; Wiley: New York, 1941, 78.
52. López, S. N.; Castelli, M. V.; Azcchino, S. A.; Domínguez, J. N.; Lobo, G.; Charris-Charris, J.; Cortés, J. C. G.; Ribas, J. C.; Devia, C.; Rodríguez, A. M.; Enriz, R. D. Bioorg. Med. Chem. 2001, 9, 1999.
53. Silver, N. L.; Boykin, D. W. Jr. J. Org. Chem. 1970, 35, 759.
54. Available from Syncom