Mathematical Description of Kinetic Resolution with an Enantiomerically Impure Catalyst and Nonracemic Substrate

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3772-3774

  Ismagilov, Rustern F ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001270624     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972299i     Document Type: Article

References (27)

1. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. Am. Chem. Soc. 1990, 112, 4942. Guo, Z.-W. J. Org. Chem. 1993, 58, 5748. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
2. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. Am. Chem. Soc. 1990, 112, 4942. Guo, Z.-W. J. Org. Chem. 1993, 58, 5748. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
3. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. Am. Chem. Soc. 1990, 112, 4942. Guo, Z.-W. J. Org. Chem. 1993, 58, 5748. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
4. Sih, C. J.; Wu, S.-H. Top. Stereochem. 1989, 19, 63. Guo, Z.-W.; Wu, S.-H.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. Am. Chem. Soc. 1990, 112, 4942. Guo, Z.-W. J. Org. Chem. 1993, 58, 5748. Klibanov, A. M. Acc. Chem. Res. 1990, 23, 114.
5. For recent examples, see: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (b) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499. Fujimura, O.; De la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (d) Hashiguchi, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288. (e) Vedejs, E.; Chen, X. H. J. Am. Chem. Soc. 1996, 118, 1809.
6. For recent examples, see: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (b) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499. Fujimura, O.; De la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (d) Hashiguchi, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288. (e) Vedejs, E.; Chen, X. H. J. Am. Chem. Soc. 1996, 118, 1809.
7. For recent examples, see: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (b) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499. Fujimura, O.; De la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (d) Hashiguchi, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288. (e) Vedejs, E.; Chen, X. H. J. Am. Chem. Soc. 1996, 118, 1809.
8. For recent examples, see: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (b) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499. Fujimura, O.; De la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (d) Hashiguchi, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288. (e) Vedejs, E.; Chen, X. H. J. Am. Chem. Soc. 1996, 118, 1809.
9. For recent examples, see: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (b) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499. Fujimura, O.; De la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (d) Hashiguchi, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288. (e) Vedejs, E.; Chen, X. H. J. Am. Chem. Soc. 1996, 118, 1809.
10. For recent examples, see: (a) Tokunaga, M.; Larrow, J. F.; Kakiuchi, F.; Jacobsen, E. N. Science 1997, 277, 936. (b) Fujimura, O.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 2499. Fujimura, O.; De la Mata, F. J.; Grubbs, R. H. Organometallics 1996, 15, 1865. (c) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492. (d) Hashiguchi, S.; Fujii, A.; Haack, K. J.; Matsumura, K.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 288. (e) Vedejs, E.; Chen, X. H. J. Am. Chem. Soc. 1996, 118, 1809.
11. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249. Kagan, H. B. Recl. Trav. Chim. Pays-Bas 1995, 114, 203.
12. Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249. Kagan, H. B. Recl. Trav. Chim. Pays-Bas 1995, 114, 203.
13. For example, see ref 2b.
14. (a) Brandt, J.; Jochum, C.; Ugi, I. Tetrahedron 1977, 33, 1353.
15. (b) Dynamic kinetic resolution: Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. Kitamura, M.; Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853.
16. (b) Dynamic kinetic resolution: Noyori, R.; Tokunaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36. Kitamura, M.; Tokunaga, M.; Noyori, R. Tetrahedron 1993, 49, 1853.
17. (c) Meso/dl stereoisomeric mixtures: Ward, D. E.; How, D.; Liu, Y. J. Am. Chem. Soc. 1997, 119, 1884 and references therein,
18. (d) Sequential kinetic resolution: Baba, S. E.; Sartor, K.; Poulin, J.-C.; Kagan, H. B. Bull. Soc. Chem. Fr. 1994, 131, 525.
19. (e) Kinetic analysis by progress curve evaluation: Rakels, J. L. L.; Romein, B.; Straathof, A. J. J.; Heijnen, J. J. Biotechnol. Bioeng. 1994, 43, 411. See also: Lu, Y.; Zhao, X.; Chen, Z.-N. Tetrahedron: Asymmetry 1995, 6, 1093.
20. (e) Kinetic analysis by progress curve evaluation: Rakels, J. L. L.; Romein, B.; Straathof, A. J. J.; Heijnen, J. J. Biotechnol. Bioeng. 1994, 43, 411. See also: Lu, Y.; Zhao, X.; Chen, Z.-N. Tetrahedron: Asymmetry 1995, 6, 1093.
21. x catalyst: Kagan, H. B.; Girard, C.; Guillaneux, D.; Rainford, D.; Samuel, O.; Zhang, S. Y.; Zhao, S. H. Acta Chem. Scand. 1996, 50, 345; Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934 and references therein.
22. x catalyst: Kagan, H. B.; Girard, C.; Guillaneux, D.; Rainford, D.; Samuel, O.; Zhang, S. Y.; Zhao, S. H. Acta Chem. Scand. 1996, 50, 345; Blackmond, D. G. J. Am. Chem. Soc. 1997, 119, 12934 and references therein.
23. Trost, B. M.; Bunt, R. C. J. Am. Chem. Soc. 1996, 118, 235. Approximate treatment was used.
24. SMf.
25. Chen, C.-S., Fujimoto, Y., Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. Wang, Y.-F.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1984, 106, 3695.
26. Chen, C.-S., Fujimoto, Y., Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294. Wang, Y.-F.; Chen, C.-S.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1984, 106, 3695.
27. Note that there is a typographical error in eq 12 of ref 3 - the minus sign in the numerator of the left fraction should be changed to a plus sign, as it is here and in ref 8.