Reactions of aldehydes with diethylzinc catalysed by polymersupported ephedrine and camphor derivatives: Comparisons of enantiomeric excesses achieved with various supports: optimisation of support parameters to enable high enantiomeric excesses to be obtained f

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1999, Pages 1463-1472

  Sung, David W L ^a   Hodge, Philip ^a   Stratford, Peter W ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b LANCASTER UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004751494     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901455a     Document Type: Article

References (46)

1. R. B. Merrifield, J. Am. Chem. Soc., 1963, 85, 2149.
2. Polymer-supported Reactions in Organic Synthesis, eds. P. Hodge and D. C. Sherrington, John Wiley, Chichester, 1980.
3. Polymeric Reagents and Catalysts, ed. W. T. Ford, ACS Symposium Series 308, Washington, 1986.
4. Syntheses and Separations Using Functional Polymers, eds. D. C. Sherrington and P. Hodge, John Wiley, Chichester, 1988.
5. A. Akelah and A. Moet, Functionalised Polymers and Their Applications, Chapman and Hall, London, 1990.
6. A. Akelah and D. C. Sherrington, Chem, Rev., 1981, 81, 557.
7. A. Akelah and D. C. Sherrington, Polymer, 1983, 24, 1369.
8. P. Hodge, Anna. Rep. Prog. Chem., Sect. B, Org. Chem., 1986, 283.
9. P. Hodge, Chem. Soc. Rev., 1997, 26, 417.
10. C. Dreisbach, G. Wischnewski, U. Kragl and C. Wandrey, J. Chem. Soc, , Perkin Trans, l, 1995, 875.
11. IIP. Hodge, in Innovation and Perspectives in Solid Phase Synthesis, ed. R. Epton, SPCC (UK) Ltd., Birmingham, 1990, pp. 273-292.
12. R. Noyori, Asymmetrie Catalysis in Organic Synthesis, John Wiley, New York, 1994.
13. G. Liu and J. A. Ellman, J. Org. Chem., 1995, 60, 7712.
14. S. R. Gilbertson and X. Wang, Tetrahedron Lett., 1996, 37, 6475.
15. B. M. Cole, K. D. Shimizu, C. A. Knieger, J. P. A. Harrity, M. L. Snapper and A. H. Horveyda, Angew. Chem., Int. Ed. Engl, 1996, 35, 1668.
16. S. Itsuno and J. M. J. Frechet, J. Org. Chem., 1987, 52, 4140.
17. K. Soai, S. Niwa and M. Watanabe, J Org. Chem., 1988, 53, 927.
18. K. Soai, S. Niwa and M. Watanabe, J. Chem. Soc, , Perkin Trans, l, 1989, 109.
19. K.- Soai and M. Watanabe, J. Chem. Soc., Chem. Commun., 1990, 43.
20. S. Itsuno, Y. Sakurai, K.. Ito, T. Maruyama, S. Nakahama and J. M. J. Frechet, J. Org. Chem., 1990, 55, 304.
21. M. Watanabe, S. Araki, Y. Butsugan and M. Uemura, Chem. Express, 1990, 5, 761.
22. Z. Zhang, P. Hodgeand P. W. Stratford, React. Polyin., 1991, 15, 71.
23. M. Watanabe and K. Soai, J. Chem. Soc., Perkin Trans, l, 1994, 837. '
24. D. Seebach, R. E. Marti and T. Hintermann, Helv. Chim. Acta, 1996, 79, 1710.
25. K. Soai and S. Niwa, Chem. Rev., 1992, 92, 833.
26. K. Soai, M. Watanabe and A. Yamamoto, J. Org. Chem., 1990, 55, 4832.
27. K. Burgess and D. Lim, Chem. Commun., 1997, 785.
28. L. Canali, E. Cowan, H. Deleuze, C. L. Gibson and D. C. Sherrington, Chem. Commun., 1998, 2561. :
29. M. Kitamura, S. Okada, S. Suga and R. Noyori, J. Am. Chem. Soc., 1989, 111, 4028.
30. R. Noyori and M. Kitamura, Angew. Chem., Int. Ed. Engl., 1991, 30, 49.
31. G. E. Coates and D. Ridley, J. Chem. Soc. (A), 1966, 1064.
32. P. A. Chaloner and E. Langadianou, Tetrahedron Lett., 1990, 31, 5185.
33. N. Oguni and T. Omi, Tetrahedron Lett., 1984, 25, 2823.
34. A. H. Alberts and H. Wynberg, J. Am. Chem. Soc., 1989, 111, 7264.
35. D. J. Gravert and D. K. Janda, Chem. Rev., 1997, 97, 489.
36. F. Villedon-Denaide, P. Lecavalier and J. M. J. Frechet, Polym. Bull., 1986, 15, 491.
37. B. Marx, E. Henry-Basch and P. Freon, C. R. Seances Acad. Sci., Ser. C, 1967, 264, 1967.
38. D. C. Sherrington, Chem. Commun., 1998, 2275.
39. N. R. Cameron and D. C. Sherrington, Adv. Pol. Sci., 1996, 126, 163.
40. M. Kitamura, S. Suga, K. Kawai and R. Noyori, J. Am. Chem. Soc., 1986, 108, 6071.
41. R. Noyori, S. Suga, K. Kawai, S. Okada, M. Kitamura, N. Oguni, M. Hayashi, T. Kaneko and Y. Matsuda, J. Organomet. Chem, 1990, 382, 19.
42. R. H. Pickard and J. Kenyon, J. Chem. Soc., 1914, 1115.
43. J. Capillonand J. Guette, Tetrahedron, 1979, 35, 1817.
44. A. A. Smaardijk and H. Wynberg, J. Org. Chem., 1987, 52, 135.
45. M. P. Bonner and E. R. Thornton, J. Am. Chem. Soc, , 1991, 113, 1299.
46. R. M. Chittenden and G. H. Cooper, J. Chem. Soc(C), 1970, 49.