Development of the Juliá-Colonna asymmetric epoxidation reaction: Part 1. Preparation and activation of the polyleucine catalyst

Organic Process Research and Development

Volumn 7, Issue 4, 2003, Pages 509-513

  Baars, Sylvia ^a   Drauz, Karl Heinz ^b   Krimmer, Hans Peter ^b   Roberts, Stanley M ^a   Sander, Jörg ^a   Skidmore, John ^a   Zanardi, Giampaolo ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b EVONIK INDUSTRIES AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

LEUCINE; POLYAMINOACID; SILICON DIOXIDE;

ARTICLE; CATALYST; EPOXIDATION;

EID: 0041743964     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0300037     Document Type: Article

References (30)

1. Jacobsen, E. N.; Flats, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer-Verlag: Berlin and Heidelberg, 1999.
2. Johnson, R. A.; Sharpless, K. B. In Asymmetric Oxidation: Catalytic Asymmetric Epoxidation of Allylic Alcohols; Ojima, I., Ed.; VCH: New York, 1993; pp 103-158.
3. Jacobsen, E. N. Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L. S., Eds.; Pergamon: New York, 1995; Vol. 12, pp 1097-1135.
4. Porter, M. J.; Skidmore, J. Chem Commun. 2000, 1215; see also: Chen, R.; Qian, C.; de Vries, J. G. Tetrahedron Lett. 2001, 42, 6019-6022.
5. Porter, M. J.; Skidmore, J. Chem Commun. 2000, 1215; see also: Chen, R.; Qian, C.; de Vries, J. G. Tetrahedron Lett. 2001, 42, 6019-6022.
6. Juliá, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annuziata, R.; Molinari, H. J. Chem. Soc., Perkin Trans. 1 1982, 1317-1324; the triphasic protocol has been used on a large scale, see: Flisak, J. R.; Gombatz, K. J.; Holmes, M. M.; Jarmas, A. A.; Lantos, I.; Mendelson, W. L.; Novack, V. J.; Remich, J. J.; Snyder, L. J. Org. Chem. 1993, 58, 6247-6254.
7. Juliá, S.; Guixer, J.; Masana, J.; Rocas, J.; Colonna, S.; Annuziata, R.; Molinari, H. J. Chem. Soc., Perkin Trans. 1 1982, 1317-1324; the triphasic protocol has been used on a large scale, see: Flisak, J. R.; Gombatz, K. J.; Holmes, M. M.; Jarmas, A. A.; Lantos, I.; Mendelson, W. L.; Novack, V. J.; Remich, J. J.; Snyder, L. J. Org. Chem. 1993, 58, 6247-6254.
8. Lauret, C.; Roberts, S. M. Aldrichimica Acta 2002, 35, 47-51.
9. Allen, J. V.; Drauz, K. H.; Flood, R. W.; Roberts, S. M.; Skidmore, J. Tetrahedron Lett. 1999, 40, 5417-5420.
10. Geller, T. P.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1999, 1397-1398.
11. Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145-2156.
12. Bentley, P. A.; Bickley, J. F.; Roberts, S. M.; Steiner, A. Tetrahedron Lett. 2001, 42, 3741-3743.
13. Bulman-Page, P. C.; Rassias; G. A.; Barros, D.; Ardakani, A.; Buckley, B.; Bethell, D.; Smith, T. A. D.; Slawin, A. M. Z.; J. Org. Chem. 2001, 66, 6926.
14. Adger, B. M.; Barkley, J. V.; Bergeron, S.; Cappi, M. W.; Flowerdew, B. E.; Jackson, M. P.; McCague, R.; Nugent, T. C.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1997, 3501-3507.
15. Cappi, M. W.; Chen, W.-P.; Flood, R. W.; Liao, Y.-W.; Roberts, S. M.; Skidmore, J.; Smith, J. A.; Williamson, N. M. Chem. Commun. 1998, 1159-1160.
16. Carde, L.; Davies, H.; Geller, T. P.; Roberts, S. M. Tetrahedron Lett. 1999, 40, 5421-5424; Carde, L.; Davies, D. H.; Roberts, S. M. J. Chem. Soc., Perkin. Trans. 1, 2000, 2455; Chen, W. P.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1999, 103.
17. Carde, L.; Davies, H.; Geller, T. P.; Roberts, S. M. Tetrahedron Lett. 1999, 40, 5421-5424; Carde, L.; Davies, D. H.; Roberts, S. M. J. Chem. Soc., Perkin. Trans. 1, 2000, 2455; Chen, W. P.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1999, 103.
18. Carde, L.; Davies, H.; Geller, T. P.; Roberts, S. M. Tetrahedron Lett. 1999, 40, 5421-5424; Carde, L.; Davies, D. H.; Roberts, S. M. J. Chem. Soc., Perkin. Trans. 1, 2000, 2455; Chen, W. P.; Roberts, S. M. J. Chem. Soc., Chem. Commun. 1999, 103.
19. Savizky, R. M.; Suzuki, N.; Bove, J. L. Tetrahedron: Asymmetry 1998, 9, 3967-3969 and references therein.
20. Dhanda, A.; Drauz, K.-H.; Geller, T. P.; Roberts, S. M. Chirality 2000, 12, 313.
21. Kricheldorf, H. R. α-Amino acid-N-Carboxy Anhydrides and Related Heterocycles; Springer-Verlag: Berlin, 1987; see also: Bailey, J. L. J. Chem. Soc. 1950, 3461; Coleman, D. J. Chem. Soc. 1950, 3222; Grimshaw, J.; Perera, S. D. J. Chem. Soc., Perkin Trans. 2 1989, 1711.
22. Kricheldorf, H. R. α-Amino acid-N-Carboxy Anhydrides and Related Heterocycles; Springer-Verlag: Berlin, 1987; see also: Bailey, J. L. J. Chem. Soc. 1950, 3461; Coleman, D. J. Chem. Soc. 1950, 3222; Grimshaw, J.; Perera, S. D. J. Chem. Soc., Perkin Trans. 2 1989, 1711.
23. Kricheldorf, H. R. α-Amino acid-N-Carboxy Anhydrides and Related Heterocycles; Springer-Verlag: Berlin, 1987; see also: Bailey, J. L. J. Chem. Soc. 1950, 3461; Coleman, D. J. Chem. Soc. 1950, 3222; Grimshaw, J.; Perera, S. D. J. Chem. Soc., Perkin Trans. 2 1989, 1711.
24. Kricheldorf, H. R. α-Amino acid-N-Carboxy Anhydrides and Related Heterocycles; Springer-Verlag: Berlin, 1987; see also: Bailey, J. L. J. Chem. Soc. 1950, 3461; Coleman, D. J. Chem. Soc. 1950, 3222; Grimshaw, J.; Perera, S. D. J. Chem. Soc., Perkin Trans. 2 1989, 1711.
25. Katakai, R.; Iizuka, Y. J. Org. Chem. 1985, 50, 715-716.
26. Daly, W. H.; Poche', D. Tetrahedron Lett. 1988, 29, 5859-5862.
27. Kricheldorf, H. R.; Müller, D. Int. J. Biol. Macromol. 1983, 5, 171.
28. Itsuno, S.; Sakakura, M.; Ito, K. J. Org. Chem. 1990, 55, 6047-6049.
29. Heller, J.; Heller, A., J. Am. Chem. Soc. 1998, 120, 4586 and references therein.
30. Song, C. E.; Oh, C. R.; Lee, S. W.; Lee, S.; Canali, L.; Sherrington, D. C. Chem. Commun. 1998, 2435.