Bifunctional catalysts for catalytic asymmetric sulfur ylide epoxidation of carbonyl compounds

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 13, 1998, Pages 2037-2042

  Aggarwal, Varinder K ^a   Bell, Louise ^a   Coogan, Michael P ^a   Jubault, Philippe ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748637615     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a802362j     Document Type: Article

References (24)

1. R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. A. Ojima, VCH, New York, 1993, p. 103.
2. T. Katsuki and V. S. Martin, Org. React., 1996, 48, 1.
3. T. Katsuki, Coord. Chem. Rev., 1995, 140, 189.
4. E. N. Jacobsen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, New York, 1993, p. 159.
5. Z.-W. Wang, Y. Tu, M. Frohn, J.-R. Zhang and Y. Shi, J. Am. Chem. Soc., 1997, 119, 11224.
6. V. K. Aggarwal, H. Abdel-Rahman, L. Fan, R. V. H. Jones and M. C. H. Standen, Chem. Eur. J., 1996, 2, 212.
7. V. K. Aggarwal, J. G. Ford, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Am. Chem. Soc., 1996, 118, 7004.
8. A. Pfaltz, Acc. Chem. Res., 1993, 26, 339.
9. A. Pfaltz, Acta Chem. Scand., 1996, 50, 189.
10. R. E. Lowenthal, A. Abiko and S. Masamune, Tetrahedron Lett., 1990, 31, 6005.
11. R. E. Lowenthal and S. Masamune, Tetrahedron Lett., 1991, 32, 7373.
12. D. Müller, G. Umbricht, B. Weber and A. Pfaltz, Helv. Chim. Acta, 1991, 74, 232.
13. D. A. Evans, K. A. Woerpal, M. M. Hinman and M. M. Faul, J. Am. Chem. Soc., 1991, 113, 726.
14. D. A. Evans, K. A. Woerpel and M. J. Scott, Angew. Chem., Int. Ed. Engl., 1992, 31, 430.
15. H. Seki, K. Koga, H. Matsuo, S. Ohki, I. Matsuo and S. Yamada, Chem. Pharm. Bull., 1965, 13, 995.
16. D. A. Dickman, A. I. Meyers, G. A. Smith and R. E. Gawley, Org. Synth., 1990, Coll. Vol. VII, 530.
17. This amino alcohol is commercially available.
18. J. Hall, J.-M. Lehn, A. Decian and J. Fischer, Helv. Chim. Acta, 1991, 74, 1.
19. G. Koch, Dissertation Thesis University of Basel, 1995.
20. See also: H. Witte and W. Seeliger, Liebigs Ann. Chem., 1974, 996. We thank Prof. A. Pfaltz for bringing this method to our attention.
21. 2 has also been used as a catalyst for this type of transformation: C, Bolm, K. Weickhardt, M. Zehnder and T. Ranff, Chem. Ber., 1991, 124, 1173;
22. M. Nakamura, A. Hirai and E. Nakanmura, J. Am. Chem. Soc., 1996, 118, 8489. However, we observed only partial formation of the bisoxazolines (formation of the non-symmetrical oxazoline).
23. R. G. Salomon and J. K. Kochi, J. Am. Chem. Soc., 1973, 95, 3300.
24. G. J. Kubas, B. Monzyk and A. L. Crumbliss, Inorg. Synth., 1979, 19, 90.