The design of novel N-4′-pyridinyl-α-methyl proline derivatives as potent catalysts for the kinetic resolution of alcohols

Journal of Organic Chemistry

Volumn 68, Issue 10, 2003, Pages 3844-3848

  Priem, Ghislaine ^a   Pelotier, Béatrice ^a   Macdonald, Simon J F ^a   Anson, Mike S ^a   Campbell, Ian B ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; CATALYSIS; HYDROGEN BONDS; SUBSTRATES;

CHIRAL ACYLATION CATALYSTS;

ORGANIC COMPOUNDS;

ACID ANHYDRIDE; ALCOHOL; ETHANOLAMINE DERIVATIVE; N 4' PYRIDINYL ALPHA METHYLPROLINE DERIVATIVE; PROLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CHIRALITY; ENANTIOSELECTIVITY; HYDROGEN BOND;

EID: 0037613400     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026485m     Document Type: Article

References (39)

1. (a) Litvinenko, L. M.; Kirichenko, A. I. Chem. Abstr. 1968, 68, 68325u.
2. (b) Höfle, G.; Steglich, W.; Vorbrüggen, H. Angew. Chem., Int. Ed. Engl. 1978, 17, 569.
3. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2001, 40, 3726.
4. Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 11532.
5. (a) Hodous, B. L.; Ruble, J. C.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 2637.
6. (b) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091.
7. (c) Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 10452.
8. (d) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230.
9. (a) Spivey, A. C.; Maddaford, A.; Leese, D. P.; Redgrave, A. J. J. Chem. Soc., Perkin Trans. 1 2001, 1785.
10. (b) Spivey, A. C.; Maddaford, A.; Fekner, T.; Redgrave, A.; Frampton, J. C. S. J. Chem. Soc., Perkin Trans. 1 2000, 3460.
11. (c) Spivey, A. C.; Fekner, T.; Spey, S. E. J. Org. Chem. 2000, 65, 3154.
12. (d) Spivey, A. C.; Fekner, T.; Adams, H. Tetrahedron Lett. 1998, 39, 8919.
13. (e) Spivey, A. C.; Charbonneau, P.; Fekner, T.; Hochmuth, D. H.; Maddaford, A.; Malardier-Jugroot, C.; Redgrave, A. J.; Whitehead, M. A. J. Org. Chem. 2001, 66, 7394.
14. (f) Spivey, A. C.; Fekner, T.; Spey, S. E.; Adams, H. J. Org. Chem. 1999, 64, 9430.
15. Kawabata, T.; Nagato, M.; Takasu, K.; Fuji, K. J. Am. Chem. Soc. 1997, 119, 3169.
16. Kawabata, T.; Yamamoto, K.; Momose, Y.; Yoshida, H.; Nagaoka, Y.; Fuji, K. Chem. Commun. 2001, 2700.
17. Naraku, G.; Shimomoto, N.; Hanamoto, T.; Inanaga, J. Enantiomer 2000, 5, 135.
18. (a) Vedejs, E.; Rozners, E. J. Am. Chem. Soc. 2001, 123, 2428.
19. (b) Vedejs, E.; MacKay, J. A. Org. Lett. 2001, 3, 535.
20. (c) Vedejs E.; Daugulis, O. J. Am. Chem. Soc. 1999, 121, 5813.
21. (d) Vedejs, E.; Daugulis, O.; Diver, S. T. J. Org. Chem. 1996, 61, 430.
22. (a) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638.
23. (b) Copeland, G. T.; Jarvo, E. R.; Miller, S. J. J. Org. Chem. 1998, 63, 6784.
24. (c) Vasbinder, M. M.; Jarvo, E. R.; Miller, S. J. Angew. Chem., Int. Ed. 2001, 40, 2824.
25. (d) Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Hortsmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629.
26. (a) Sano, T.; Imai, K.; Ohashi, K.; Oriyama, T. Chem. Lett. 1999, 3, 265.
27. (b) Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 3529.
28. (c) Oriyama, T.; Hori, Y.; Imai, K.; Sazaki, R. Tetrahedron Lett. 1996, 37, 8543.
29. Taylor, S. J.; Morken, J. P. Science 1998, 280, 267.
30. Delaney, E. J.; Wood, L. E.; Klotz, I. M. J. Am. Chem. Soc. 1982, 104, 799.
31. Priem, G.; Anson, M. S.; Macdonald, S. J. F.; Pelotier, B.; Campbell, I. B. Tetrahedron Lett. 2002, 43, 6001.
32. The selectivity index was calculated from Kagan's rule: Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249.
33. NOEs calculated from the nonacylated and acylated forms of catalysts 8 and 17 have demonstrated no differences in NOEs whether the catalyst does or does not contain an aromatic group.
34. Note: Alcohols 38-40 have also been described by Fuji as effective substrates for enantioselective acylation reactions (>99% ee, S > 13) in refs 6 and 7.
35. (a) Spivey, A. C.; Andrews, B. I. Angew. Chem., Int. Ed. 2001, 40, 3131.
36. (b) Tang, L.; Deng, L. J. Am. Chem. Soc. 2002, 124, 2870.
37. (c) Hodous, B. L.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 1578.
38. Gomez-Vidal, J.; Forrester, M. T.; Silvermann, R. B. Org. Lett. 2001, 3, 2477.
39. Byun, Y. S.; Lightner, D. A. Tetrahedron 1991, 47, 9759.