Enantioselective synthesis of epoxides and aziridines by asymmetric methylidene transfer from a sulfimide to carbonyl compounds and imines

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1998, Pages 3399-3403

  Baird, Charlotte P ^a   Taylor, Paul C ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748511020     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a805405c     Document Type: Article

References (32)

1. Asymmetric epoxidations: R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, Section 4.1;
2. E. N. Jacobsen, in Catalytic Asymmetric Synthesis, ed. I. Ojima, VCH, Weinheim, 1993, Section 4.2.
3. Asymmetric aziridinations: D. A. Evans, M. M. Faul, M. T. Bilodeau, B. A. Anderson and D. M. Barnes, J. Am. Chem. Soc., 1993, 115, 5328;
4. Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326;
5. P. Müller, C. Baud and Y. Jacquier, Tetrahedron, 1996, 52, 1543;
6. M. J. Södergren, D. A. Alonso and P. G. Andersson, Tetrahedron: Asymmetry, 1997, 8, 3563.
7. S. E. Kelly, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, Pergamon, Oxford, 1991, Section 3.1.
8. A-H. Li, L.-X. Dai and V. K. Aggarwal, Chem. Rev., 1997, 97, 2341.
9. M. Tokunaea, J. F. Larrow, F. Kakiuchi and E. N. Jacobsen, Science, 1997, 277, 936.
10. A. Solladié-Cavallo and A. Diep-Vohuule, J. Org. Chem., 1995, 60, 3494.
11. B. M. Trost and R. F. Hammen, J. Am. Chem. Soc., 1973, 95, 962.
12. C. R. Johnson, R. A. Kirchoff, R. J. Reischer and G. F. Katekar, J. Am. Chem. Soc., 1973, 95, 4287. There is an error in the structure labelled as 4-(R) in this paper since the molecule shown is of (S) configuration.
13. S. S. Taj, A. C. Shah, D. Lee, G. Newton and R. Soman, Tetrahedron: Asymmetry, 1995, 6, 1731;
14. S. S. Taj and R. Soman, Tetrahedron: Asymmetry, 1994, 5, 1513.
15. C. P. Baird and P. C. Taylor, J. Chem. Soc., Chem. Commun., 1995, 893.
16. V. K. Aggarwal, A. Thompson, R. V. H. Jones and M. C. H. Standen, J. Org. Chem., 1996, 61, 8368.
17. A.-H. Li, Y-G. Zhou, L.-X. Dai, X.-L. Hou, L.-J. Xia and L. Lin, Augew. Chem., Int. Ed. Engl., 1997, 36, 1317.
18. D. J. Cram, J. Day, D. R. Rayner, D. M. von Schrilz, D. J. Duchamp and D. C. Garwood, J. Am. Chem. Soc., 1970, 92, 7369.
19. G. Celentano, S. Colonna, N. Gaggero and C. Richelmi, Chem. Commun., 1998, 701.
20. L. A. Bigelow and H. Eatough, Org. Synth., 1941, 1, 80;
21. W. B. Jennings and C. J. Lovely, Tetrahedron Lett., 1988, 29, 3725.
22. (a) Y. Tamura, H. Matsushima and M. Ikeda, Synthesis, 1976, 35;
23. (b) Y. Tamura, S. M. Bayomi, K. Sumoto and M. Ikeda, Synthesis, 1977, 693;
24. (c) C. R. Johnson, K. Mori and A. Nakanishi, J. Org. Chem., 1979, 2065.
25. A. J. Pearson, S. L. Blystone, H. Nar, A. A. Pinkerton, B. A. Roden and J. Y. Yoon, J. Am. Chem. Soc., 1989, 111, 134.
26. A. Solladié-Cavallo and M. Bencheqroun, J. Org. Chem., 1992, 57, 5831; we used a modified procedure described by the same group in Solladié-Cavallo, ref. 6 above.
27. S. K. Taylor, G. H. Hockerman, G. L. Karrick, S. B. Lyle and S. B. Schramm, J. Org. Chem., 1983, 48, 2449.
28. N. Krause and D. Seebach, Chem. Ber., 1988, 121, 1315.
29. M. Alvarez, R. Granados, R. Lavilla and M. Salas, J. Heterocycl. Chem., 1985, 22, 745.
30. E. Liepins, V. A. Pestunovich, A. V. Eremeev, D. A. Tikhomirov and N. P. Gaidarova, Khim. Geterotsikl. Soedin., 1977, 906
31. (Chem. Abstr., 1977, 87, 183795b).
32. US 3281468 (Chem. Abstr., 1967, 67, 11329y).