The family approach to the resolution of racemates

Angewandte Chemie - International Edition

Volumn 37, Issue 17, 1998, Pages 2349-2354

  Vries, Ton ^a   Wynberg, Hans ^a   Van Echten, Erik ^a   Koek, Jan ^a   Ten Hoeve, Wolter ^a   Kellogg, Richard M ^a   Broxterman, Quirinus B ^b   Minnaard, Adri ^b   Kaptein, Bernard ^b   Van Der Sluis, Sietse ^c   Hulshof, Lumbertus ^c   Kooistra, Jaap ^c  

^a Syncom BV   (Netherlands)

^b DSM RESEARCH   (Netherlands)

^c NONE   (Netherlands)

Author keywords

Chiral resolution; Chirality; Combinatorial chemistry; Enantiomeric resolution

Indexed keywords

EID: 0032544370     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980918)37:17<2349::AID-ANIE2349>3.0.CO;2-I     Document Type: Article

References (25)

1. L. Pasteur, Ann. Chim. Phys. 1848, 24, 442-459.
2. L. Pasteur, C. R. Hebd. Seances Acad. Sci. 1853, 37, 162-169.
3. Comprehensive books on stereochemistry encompassing these 150 years: K. Freudenberg, Stereochemie, F. Deuticke, Leipzig, 1932; E. L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962; J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley-Interscience, New York, 1981; E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994; the most complete description of the resolution of racemates (167 pages of chapter 7) can be found in the latter book.
4. Comprehensive books on stereochemistry encompassing these 150 years: K. Freudenberg, Stereochemie, F. Deuticke, Leipzig, 1932; E. L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962; J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley-Interscience, New York, 1981; E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994; the most complete description of the resolution of racemates (167 pages of chapter 7) can be found in the latter book.
5. Comprehensive books on stereochemistry encompassing these 150 years: K. Freudenberg, Stereochemie, F. Deuticke, Leipzig, 1932; E. L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962; J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley-Interscience, New York, 1981; E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994; the most complete description of the resolution of racemates (167 pages of chapter 7) can be found in the latter book.
6. Comprehensive books on stereochemistry encompassing these 150 years: K. Freudenberg, Stereochemie, F. Deuticke, Leipzig, 1932; E. L. Eliel, Stereochemistry of Carbon Compounds, McGraw-Hill, New York, 1962; J. Jacques, A. Collet, S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley-Interscience, New York, 1981; E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994; the most complete description of the resolution of racemates (167 pages of chapter 7) can be found in the latter book.
7. R. A. Sheldon, Chirotechnology, Marcel Dekker, New York, 1993, chap. 6.
8. A. D. van der Haest, H. Wynberg, Recl. Trav. Chim. Pays-Bas 1992 111, 111-118; A. D. van der Haest, H. Wynberg, F. J. J. Leusen, H. J. Bruins, J. H. Noordik, A. Bruggink, Recl. Trav. Chim. Pays-Bas 1991, 110, 13-18.
9. A. D. van der Haest, H. Wynberg, Recl. Trav. Chim. Pays-Bas 1992 111, 111-118; A. D. van der Haest, H. Wynberg, F. J. J. Leusen, H. J. Bruins, J. H. Noordik, A. Bruggink, Recl. Trav. Chim. Pays-Bas 1991, 110, 13-18.
10. R. O. Gould, M. D. Walkinshaw, J. Am. Chem. Soc. 1984, 106, 7840-7842; R. O. Gould, A. M. Gray, P. Taylor, M. D. Walkinshaw, J. Am. Chem. Soc. 1985, 107, 5921-5927. This paper specifically uses the term "a small family of related crystal structures" in discussing nonbonding interactions. To our understanding the word "family" already implies a relationship. See also R. O. Gould, R. Kelly, M. D. Walkinshaw, J. Chem. Soc. Perkin. Trans. 2 1985, 847-852.
11. R. O. Gould, M. D. Walkinshaw, J. Am. Chem. Soc. 1984, 106, 7840-7842; R. O. Gould, A. M. Gray, P. Taylor, M. D. Walkinshaw, J. Am. Chem. Soc. 1985, 107, 5921-5927. This paper specifically uses the term "a small family of related crystal structures" in discussing nonbonding interactions. To our understanding the word "family" already implies a relationship. See also R. O. Gould, R. Kelly, M. D. Walkinshaw, J. Chem. Soc. Perkin. Trans. 2 1985, 847-852.
12. R. O. Gould, M. D. Walkinshaw, J. Am. Chem. Soc. 1984, 106, 7840-7842; R. O. Gould, A. M. Gray, P. Taylor, M. D. Walkinshaw, J. Am. Chem. Soc. 1985, 107, 5921-5927. This paper specifically uses the term "a small family of related crystal structures" in discussing nonbonding interactions. To our understanding the word "family" already implies a relationship. See also R. O. Gould, R. Kelly, M. D. Walkinshaw, J. Chem. Soc. Perkin. Trans. 2 1985, 847-852.
13. S. P. Zingg, E. M. Arnett, A. T. McPhail, A. A. Bother-By, W. R. Gilkerson, J. Am. Chem. Soc. 1988, 110, 1565-1580; A. D. van der-Haest, H. Wynberg, F. J. J. Leusen, A. Bruggink, Recl. Trav. Chim. Pays-Bas 1990, 109, 523-528.
14. S. P. Zingg, E. M. Arnett, A. T. McPhail, A. A. Bother-By, W. R. Gilkerson, J. Am. Chem. Soc. 1988, 110, 1565-1580; A. D. van der-Haest, H. Wynberg, F. J. J. Leusen, A. Bruggink, Recl. Trav. Chim. Pays-Bas 1990, 109, 523-528.
15. E. Fogassi, F. Faigl, M. Acs, K. Simon, E. Kozsda, B. Podányi, M. Czugler, G. Reck, J. Chem. Soc. Perkin Trans 2 1988, 1385-1392, and earlier papers.
16. Acc. Chem. Res. 1996, 29 (special issue; Eds.: A. W. Czarnik, J. A. Ellman).
17. Because of the confidential nature of much of our work, less than half of the resolutions we have carried out during the past year are listed in Tables 1 and 2. Approximately half of all of the resolutions were performed on a 3-mmol scale, whereas the other half was carried out on a 5-to 500-g scale. The enantiomeric excesses was examined in all cases, but an accurate yield was determined for the larger scale resolutions only. In the latter cases this yield was consistently above 20% (50% maximum) and frequently in the range of 40-45%, even without complete optimization. The method has been patented: T. R. Vries, H. Wijnberg, E. van Echten, L. Hulshof and Q. B. Broxterman (DSMNV), NL 1 004 346, 1996.
18. W. ten Hoeve, H. Wynberg, J. Org. Chem. 1985, 50, 4508-4514.
19. Exceptions to this generalization have already been found. Thus, when mixtures of amino acids are used as resolving agents, a single resolving agent was found in the diastereomeric salt. Substitution of the amino group of a single amino acid by various benzoyl chlorides led to formation of a "family" (PGA mix).
20. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley-Interscience, New York, 1994, pp. 329-343.
21. Tartaric acid, malic acid, and lactic acid also did not constitute a family.
22. L. Addadi, J. Van Mil, M. Lahav, J. Am. Chem. Soc. 1981, 103, 1249-1251.
23. See, for example, F. Toda, Top. Curr. Chem. 1987, 140, 43-51.
24. K. Mikami, S. Matsukawa, T. Volk, M. Terada, Angew. Chem. 1997, 109, 2936-2939; Angew. Chem. Int. Ed. Engl. 1997, 36, 2768-2771.
25. K. Mikami, S. Matsukawa, T. Volk, M. Terada, Angew. Chem. 1997, 109, 2936-2939; Angew. Chem. Int. Ed. Engl. 1997, 36, 2768-2771.