A new procedure for the Julia-Colonna stereoselective epoxidation reaction under non-aqueous conditions: The development of a catalyst comprising polyamino acid on silica (PaaSiCat)

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1999, Pages 1397-1398

  Geller, Thomas ^a   Roberts, Stanley M ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000187950     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903219c     Document Type: Article

References (22)

1. S. Banfi, S. Colonna, H. Molinari, S. Julia and J. Guixer, Tetrahedron, 1984, 40, 5207 and references cited therein;
2. reviewed by S. Ebrahim and M. Wills, Tetrahedron: Asymmetry, 1997, 7, 3163;
3. L. Pu, Tetrahedron: Asymmetry, 1998,9, 1457.
4. H. van Rensburg, P. S, Heerden, B. C. B. Bezuidcnhoudt and D. Ferreira, Tetrahedron, 1997, 53, 14141;
5. R. J. J. Niel, P. S. van Heerden, H. van Rensburg and D. Ferreira, Tetrahedron Lett., 1998, 39, 5623;
6. J. R. Falck, R. K. Bhatt, K. M. Reddy and J. Ye, Syntett, 1997,481;
7. P. W. Baures, D.S. Eggleston, J. R. Flisak, K.J. Gombatz, I. Lantos, W. L. Mendelson and J. J. Remich, Tetrahedron Lett., 1990,31,6501.
8. P. A. Bentle'y, S. Bergeron, M. W. Cappi, D. E. Hibbs, M. B. Hursthouse, T. C. Nugent, R. Pulido, S. M. Roberts and L. E. Wu, Client. Commun., 1997, 739;
9. B. M. Adger, J. V. Barkley, S. Bergeron, M. W. Cappi, B. E. Flowerdew, M. P. Jackson, R. McCague, T. C. Nugent and S. M. Roberts, J. Chem. Soc., Perkin Trans. J, 1997, 3501;
10. see also R. M. Savizky, N. Suzuki and J. L. Bové, Tetrahedron: Asymmetry, 1998,9, 3967.
11. J. V. Allen, M. W. Cappi, P. D. Kary, S. M. Roberts, N. M. Williamson and L. E. Wu, J. Chem. Soc., Perkin Trans, l, 1997, 3297;
12. for a full discussion on the range of substrates epoxidized efficiently in the two-phase system see J. V. Allen, S. M. Roberts and N. M. Williamson, Adv. Biochem. Eng.lBiotechwL, 1998,63, 125.
13. J. R. Flisak, K. J. Gombatz, M. M. Holmes, A. A. Jarmas, I. Lantos, W. L. Mendelson, V. J. Novack, J. J. Remich and L. Snyder, J. Org. Chem., 1993,58, 6247.
14. J. V. Alien, S. Bergeron, M. J. Griffiths, S. Mukherjee, S. M. Roberts, N. M. Williamson and L. E. Wu, J. Chem. Soc., Perkin Trans. J, 1998,3171.
15. For example see J. Partridge, P. J. Hailing and B. D. Moore, Chem. Commun., 1998,841 and references therein.
16. PLL was prepared according to S. Itsuno, M. Sakkura and K. Ito, J. Org. Chem., 1990, 55, 6047 and adsorbed onto the following materials: aluminium oxide (activated, neutral, Brockmann l, STD grade, 150 mesh); Celite HyfloSuperCel; CPC (375 A, 30-45 mesh); 3-aminopropyl derivatized CPC (375 A, 30-45 mesh); silica gel 60 (230-400 mesh); Wessalith Day P; molecular sieve (SiO2); molecular sieve (Na/Al silicate); zeolite TS 1 (5.5 A, 3% Ti).
17. R. Bovara, G. Carrea, L. Ferarra and S. Riva, Tetrahedron: Asym. metry, 1991,2,931. -
18. B. C. Das and J. Iqbal, Tetrahedron Lett., 1997,38, 1235.
19. Further reduction in the amount of pLL/silica employed led to a decreased rate of reaction and a drop in enantioselectivity.
20. P. A. Bentley, W. Kroutil, J. A. Littlechild and S. M. Roberts, Chirality, 1997,9, 198.
21. For example M. Bougauchi, S. Watanabe, T. Arai, H. Sasai and M. Shibasaki, J. Am. Chem. Soc., 1997, 119, 2329;
22. C. L. Elston, R. F. W. Jackson, S. J. F. MacDonald and P. J. Murray, Angew. Chem., Int. Ed. Engl, 1997,36,410.